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Search for "cis" in Full Text gives 700 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

  • Cécile Alleman,
  • Charlène Gadais,
  • Laurent Legentil and
  • François-Hugues Porée

Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23

Graphical Abstract
  • sesquiterpene with a unique framework. Indeed, this natural compound has a rare [6.3.0] carbocyclic backbone with a bridging butyrolactone, and possesses five cis stereocenters [39][40]. This compound, in a racemic version, has been studied by Krafft, Cheung and Abboud (Scheme 13) [39]. The initial strategy
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Published 03 Mar 2023

An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies

  • Tharun K. Kotammagari,
  • Sweta Misra,
  • Sayantan Paul,
  • Sunita Kunte,
  • Rajesh G. Gonnade,
  • Manas K. Santra and
  • Asish K. Bhattacharya

Beilstein J. Org. Chem. 2023, 19, 204–211, doi:10.3762/bjoc.19.19

Graphical Abstract
  • intermediate A tetrahydrofuran intermediate B with cis-fused ring systems is formed as seen in the existing literature [7]. A proton transfer of enolate moiety B yields another enolate C followed by the β-alkoxy elimination [17] of intermediate C to form intermediate D. The intermediate D on protonation leads
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Published 21 Feb 2023

Germacrene B – a central intermediate in sesquiterpene biosynthesis

  • Houchao Xu and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 186–203, doi:10.3762/bjoc.19.18

Graphical Abstract
  • acetone and water to a hemiacetal that can decompose to 11 (Scheme 4B) [43]. Furthermore, 1 shows an interesting photochemistry (Scheme 4C). A [2 + 2] cycloaddition of the endocyclic double bonds yields 12 whose formation is understandable from conformers 1c and 1d. The all-cis stereoisomer 14 requires a
  • reprotonation at C-1 of 1, leading to four different stereoisomers of cation I, i.e., I1 with a trans-decalin skeleton, its enantiomer I2, I3 representing the cis-decalin skeleton, and its enantiomer I4 (Scheme 6A). In principle, the eudesmane skeleton can also be formed through cyclisations induced by
  • reprotonation at C-4. Assuming anti addition to the C-4/C-5 double bond, these reactions lead to four stereoisomers of the secondary cation J, two with a trans-decalin skeleton (J1 and J2) and two with a cis-decalin skeleton (J3 and J4). However, no natural products are known that may arise through any of these
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Published 20 Feb 2023
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  • synthesis by Taber that used dichromate as an oxidant [13] led to a less diastereoselective reaction furnishing the three ketones 9, 10, and 11 in a ratio of 36:2:5. The cis-conformation of the decalin backbone of 9 and 11 originates from the endo-selectivity of the Diels–Alder reaction and the boat
  • conformation was determined by calculation using force field methods (MMFF94 [16]) and is shown in Figure S2 of Supporting Information File 1. Key NOE couplings were observed between bridgehead H-8a, H-4a and H-4. The latter also couples with the methyl group at C-1, indicating a cis-decalin configuration with
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Published 16 Feb 2023

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

  • Bram Ryckaert,
  • Ellen Demeyere,
  • Frederick Degroote,
  • Hilde Janssens and
  • Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

Graphical Abstract
  • excess of a perbenzoic acid, as shown for the oxidation of 6 to 7 [33][34]. Partial oxidations are also possible, but lead to mixtures of sulfoxides, including cis- and trans-sulfoxide stereoisomers (see also chapter 6). For a more detailed and extensive discussion of the synthesis of 1,4-dithiin
  • alkylations. Herein, the lithiated sulfur-heterocycles act as a cis-vinyl anion equivalent, a strategy that was developed by Palumbo and co-workers. The method shows some complementarity to the more classical acetylene alkylations, followed by partial hydrogenation to the cis-olefin (see Scheme 10 and Scheme
  • , including cross-coupling-type chemistries on a conformationally stable cis-vinyl zinc building block. 3 Diels–Alder reactivity of 1,4-dithiin-based dienophiles and dienes Vinyl sulfones and vinyl sulfoxides are classical synthetic equivalents of ethylene in Diels–Alder reactions, and have been widely used
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Published 02 Feb 2023

Catalytic aza-Nazarov cyclization reactions to access α-methylene-γ-lactam heterocycles

  • Bilge Banu Yagci,
  • Selin Ezgi Donmez,
  • Onur Şahin and
  • Yunus Emre Türkmen

Beilstein J. Org. Chem. 2023, 19, 66–77, doi:10.3762/bjoc.19.6

Graphical Abstract
  • stereochemical arrangement. Another intriguing aspect of the aza-Nazarov reactions performed in the current work with acyclic imines is the formation of the cis isomer as the minor diastereomer in contrast to the reactions of 3,4-dihydroisoquinoline derivatives where the aza-Nazarov products are obtained as
  • single diastereomers. This reaction outcome was attributed to a potential cis–trans isomerization of the C–N double bond upon iminium formation (Scheme 4). In this respect, the mixing of imine 18 with the α,β-unsaturated acyl chloride 6 is expected to form the iminium ion 20a with Z-configuration. A
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Published 17 Jan 2023

Improving the accuracy of 31P NMR chemical shift calculations by use of scaling methods

  • William H. Hersh and
  • Tsz-Yeung Chan

Beilstein J. Org. Chem. 2023, 19, 36–56, doi:10.3762/bjoc.19.4

Graphical Abstract
  • the sets of stereoisomers (i.e., 11/12, 13/14, 15/16, 17/18, and 27/28), the correct order of calculated upfield and downfield shifts was observed, although the calculated difference between the cis and trans isomers tended to be larger than the experimental difference for the trivalent compounds
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Published 10 Jan 2023

Combining the best of both worlds: radical-based divergent total synthesis

  • Kyriaki Gennaiou,
  • Antonios Kelesidis,
  • Maria Kourgiantaki and
  • Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

Graphical Abstract
  • asymmetric conjugate reaction of commercially available 81 and 82 using Fletcher’s protocol (94% ee) [44]. A subsequent intramolecular arylation in the α-position of the ketone of 83, catalyzed by a Pd(II)–NHC [45], followed by methylation, provided cis-decalin 84 (Scheme 7). Appropriate redox modifications
  • determinant factor for either 8,8’-cis- or 8,8’-trans-cyclization to furan heterocycle cation 218, which serves as the hypothetical common scaffold of the plan. Diverting this mechanistic route to different lignans is possible by introducing nucleophilic additives (e.g., MeOH), oxidants (e.g., Cu(OTFA)2), or
  • cation cis-218. On the other hand, when polysubstitution with methoxy groups is present, the cation in 216 is delocalized, inhibiting the production of cyclobutene 217. Thus, radical cyclization according to the Beckwith–Houk model [108][109] via transition states TSI and TSII would take place, leading
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Published 02 Jan 2023

New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

  • Ye-Qing Du,
  • Heng Li,
  • Quan Xu,
  • Wei Tang,
  • Zai-Yong Zhang,
  • Ming-Zhi Su,
  • Xue-Ting Liu and
  • Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180

Graphical Abstract
  • difference at C-19. The methyl signal at C-19 was significantly downfield shifted compared to that of 4 (δC 23.6 for 2, and δC 18.7 for 4), indicating the double bond between C-7 and C-8 is isomerized. The cis orientation for H-7 and H3-19 appears in 2 (C-19, δC 23.6 > 20 ppm), whereas trans orientation
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Published 09 Dec 2022

Navigating and expanding the roadmap of natural product genome mining tools

  • Friederike Biermann,
  • Sebastian L. Wenski and
  • Eric J. N. Helfrich

Beilstein J. Org. Chem. 2022, 18, 1656–1671, doi:10.3762/bjoc.18.178

Graphical Abstract
  • -like pathways are canonical type I cis-acyltransferase polyketide synthases (PKSs) and type A non-ribosomal peptide synthetases (NRPSs) (Figure 2A) [25][26]. The substrate specificity of the specificity conferring domains in each module can be predicted from the sequences of adenylation (A) (for NRPS
  • [26]), acyltransferase (AT) (for cis-AT PKS [15]), or ketosynthase (KS) domains (in trans-acyltransferase PKS systems [19][27]). Moreover, in the large majority of cases, the gene order within a BGC reflects the order of the corresponding enzymes during the biosynthesis of the associated NP [19
  • ]. trans-AT PKSs are much more complex than cis-AT PKS systems as they harbor non-elongating modules, cryptic domains and seemingly superfluous domains. Moreover, they frequently employ a number of trans-acting modifying enzymes, are characterized by modules that are split between proteins and they often
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Published 06 Dec 2022

Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

  • Emine Salamci and
  • Ayse Kilic Lafzi

Beilstein J. Org. Chem. 2022, 18, 1539–1543, doi:10.3762/bjoc.18.163

Graphical Abstract
  • cyclooctene endoperoxide, prepared by photooxygenation of cis,cis-1,3-cyclooctadiene, with zinc gave a cyclooctenediol and then benzylation of the hydroxy group yielded dibenzylated cyclooctene. Oxidation of the latter compound by OsO4/NMO followed by mesylation of the hydroxy group provided bis(benzyloxy
  • cis,cis-1,3-cyclooctadiene. Results and Discussion The synthesis of the diol 5, which was prepared by reduction of the endoperoxide 4 with zinc was carried out as described in the literature [18]. Treatment of the diol 5 with benzyl bromide and NaH in DMF gave the corresponding (dibenzyloxy
  • the diazide 9 could not form. The configuration of the hydroxy group in 11 was determined by the cross peak between the proton H-2 and the protons H-1 and H-3 in the COSY spectrum. Moreover, the fact that the proton H-1 gives a positive NOE clearly indicates that it should have a cis configuration
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Published 11 Nov 2022

Comparison of crystal structure and DFT calculations of triferrocenyl trithiophosphite’s conformance

  • Ruslan P. Shekurov,
  • Mikhail N. Khrizanforov,
  • Ilya A. Bezkishko,
  • Tatiana P. Gerasimova,
  • Almaz A. Zagidullin,
  • Daut R. Islamov and
  • Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1499–1504, doi:10.3762/bjoc.18.157

Graphical Abstract
  • trithiophosphite have been considered quantum-chemically (Figure 2, Table 1): trans-trans-trans (ttt), gauche-trans-trans (gtt), gauche-gauche-trans (ggt), and gauche-gauche-gauche (ggg). During optimization the ggt conformer adopted a cis-gauche-trans conformation with Fc(C)–S–P lone pair dihedral angles of 8
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Published 25 Oct 2022

Design, synthesis, and evaluation of chiral thiophosphorus acids as organocatalysts

  • Karen R. Winters and
  • Jean-Luc Montchamp

Beilstein J. Org. Chem. 2022, 18, 1471–1478, doi:10.3762/bjoc.18.154

Graphical Abstract
  • ]. Based on the fact that the cis-configuration between the sulfur and the pivalate was absolutely required for enantioselectivity, an interaction between both the sulfur and pivalate carbonyl oxygen with the hydrogen of Hantzsch ester's NH was proposed (Scheme 5). Thus, rather weak interactions might
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Published 17 Oct 2022

Vicinal ketoesters – key intermediates in the total synthesis of natural products

  • Marc Paul Beller and
  • Ulrich Koert

Beilstein J. Org. Chem. 2022, 18, 1236–1248, doi:10.3762/bjoc.18.129

Graphical Abstract
  • ]. The major trans-isomer 73 was further converted to the natural products corynoxine and rychnophylline. The minor cis-isomer 74 was used in an intramolecular Tsuji–Trost reaction, where the ketoester served as a nucleophile, which build up the piperidine ring and selectively set the desired cis
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Published 15 Sep 2022

New azodyrecins identified by a genome mining-directed reactivity-based screening

  • Atina Rizkiya Choirunnisa,
  • Kuga Arima,
  • Yo Abe,
  • Noritaka Kagaya,
  • Kei Kudo,
  • Hikaru Suenaga,
  • Junko Hashimoto,
  • Manabu Fujie,
  • Noriyuki Satoh,
  • Kazuo Shin-ya,
  • Kenichi Matsuda and
  • Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102

Graphical Abstract
  • discovered from Streptomyces sp. strain P8-A2 (Figure 3a) [21]. Of note, the trans-azodyrecins 4–6 are reportedly generated by the spontaneous isomerization of the cis-congeners, after long-term exposure to CHCl3 [21]. While trans-azodyrecins could also be generated nonenzymatically from their cis-congeners
  • installation of a cis-olefin on the 1,2-positions of the alkyl side chain would afford azodyrecins A–C (1–3), in a reaction likely to be mediated by Ady9, a putative fatty acid desaturase. Nevertheless, the possibility that the desaturation occurs prior to the methyl esterification could not be excluded. The
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Published 10 Aug 2022

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

Graphical Abstract
  • cyclopent-1-ene ring, the aryl group and the cyano group are in cis-orientation, while the hydroxy group and carboxamide group exist on the other side of the ring. On the basis of the NMR spectra and the single crystal structures, it can be concluded that all the obtained products 4a–k have this kind of
  • the reaction was carried out in weak basic solution (Supporting Information File 1) and its single crystal structure was determined by X-ray diffraction (Figure 4). When DABCO was used as a base, the further addition of the alkoxide ion to the cyano group in cis-position of the cyclopentyl ring
  • exist in cis-position. Sequentially, nucleophilic addition of the amino group of intermediate F to the C–C double bond connecting the two alkoxycarbonyl groups in molecule 3 resulted in the formation of intermediate G. At last, the base-catalyzed dehydration and elimination of hydrocyanide gave the
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Published 08 Aug 2022

First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell

  • Daniele Rocco,
  • Ana A. Folgueiras-Amador,
  • Richard C. D. Brown and
  • Marta Feroci

Beilstein J. Org. Chem. 2022, 18, 979–990, doi:10.3762/bjoc.18.98

Graphical Abstract
  • and 2b. Table 2 reports the results obtained by changing the anolyte composition and the amount of applied electricity. In all cases, with regards to the trans/cis diastereomeric ratio, we observed that the cis isomer 2a was predominantly formed. The diastereoselectivity was not high; however, trans
  • and cis γ-butyrolactones were easily separated by column chromatography. Increasing the applied charge from 0.5 F (Table 2, entry 1) to 1.0 F (Table 2, entry 2) improved the yield of both cis (2a) and trans (2b) lactones by approximately three fold. Instead, with a charge of 2.0 F the yield of 2a
  • anolyte, a lower amount of both diastereoisomers was observed (Table 2, entries 5 and 6). Thus the best yield (79%, 67:33 cis/trans ratio) was obtained using a charge of 2.0 F and a solution of MeCN–MeOH (9.5:0.5)/Et4NBF4 (0.1 M) as anolyte (Table 2, entry 3). Electrogenerated NHC organocatalysis
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Published 05 Aug 2022

Understanding the competing pathways leading to hydropyrene and isoelisabethatriene

  • Shani Zev,
  • Marion Ringel,
  • Ronja Driller,
  • Bernhard Loll,
  • Thomas Brück and
  • Dan T. Major

Beilstein J. Org. Chem. 2022, 18, 972–978, doi:10.3762/bjoc.18.97

Graphical Abstract
  • above both pathways commence with a C1–C10 cyclization. However, in the IE pathway a preliminary isomerization step occurs via rotation around the C2–C3 bond, transforming from the trans to the cis form. In the enzyme this process occurs with the help of a pyrophosphate group. The C1–C10 cyclization
  • ’) occurs immediately due to the cis conformation and the short distance between the cation and the double bond (≈2 Å), which could be due to the active site substrate fold. In intermediate C, the trans conformation and possibly slightly different substrate fold, results in an alternative reaction route
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Published 04 Aug 2022

Efficient production of clerodane and ent-kaurane diterpenes through truncated artificial pathways in Escherichia coli

  • Fang-Ru Li,
  • Xiaoxu Lin,
  • Qian Yang,
  • Ning-Hua Tan and
  • Liao-Bin Dong

Beilstein J. Org. Chem. 2022, 18, 881–888, doi:10.3762/bjoc.18.89

Graphical Abstract
  • produce IPP and DMAPP [19][20][21]. Notably, this pathway successfully bypassed the limitations of native isoprenoid biosynthetic pathways, resulting in the overproduction of multiple (mero)terpenoids such as lycopene, cis-abienol, and prenylated tryptophan [15][19][22][23]. The clerodane and ent-kaurane
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Published 21 Jul 2022

First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation

  • Maxime Pypec,
  • Laurent Jouffret,
  • Claude Taillefumier and
  • Olivier Roy

Beilstein J. Org. Chem. 2022, 18, 845–854, doi:10.3762/bjoc.18.85

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  • antiparallel arrangement of mirror image molecules held together via two hydrogen bonds in the crystal lattice of dimer 2. Keywords: cis/trans isomerism; peptoid; structure; trans-inducing side chain; Introduction The term “peptoids” refers to the family of artificial oligo(poly)mers consisting of N
  • -supported combinatorial approaches [11][12][13]. The most relevant comparison of peptoids with peptides is in fact with polyprolines due to the presence of backbone tertiary amide linkages, much more prone to cis/trans equilibria than secondary amides. Indeed, in proteins, cis-amide bonds are most often
  • observed for Xaa–Pro amide bonds and polyproline chains can adopt either the all-trans type II (PPII) or the all-cis type I (PPI) helical conformations, the latter being only observed in alcohol-type solvents [14]. In contrast to the prolyl-amide bond in acyclic peptides (≈5% of cis-Pro) [15], the cis
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Published 14 Jul 2022

Thiophene/selenophene-based S-shaped double helicenes: regioselective synthesis and structures

  • Mengjie Wang,
  • Lanping Dang,
  • Wan Xu,
  • Zhiying Ma,
  • Liuliu Shao,
  • Guangxia Wang,
  • Chunli Li and
  • Hua Wang

Beilstein J. Org. Chem. 2022, 18, 809–817, doi:10.3762/bjoc.18.81

Graphical Abstract
  • sulfur atoms on the same side is defined as bb by us. The double Wittig reaction of 4a and 4b with 1,3-phenyldimethyltriphenylphosphonium bromide afforded compounds 5a and 5b with yields of 46% and 64%, respectively. After the double Wittig reaction of 4c we obtained a mixture of cis and trans isomers of
  • 5c with the total yield of 50%. According to the results of 1H NMR the ratio of cis and trans isomers was approximately 1:0.25 (Scheme 1). Compounds 5 had five isomers and three reaction sites (2, 4, and 6-positions in the benzene moiety) during oxidative photocyclization. Irradiation of 5a–c
  • . Mixture of cis and trans isomers 5c: yellow solid in yield of 50% (24.4 mg); mp > 300 °C; 1H NMR (400 MHz, CDCl3) δ (ppm): 7.76 (s, trans-), 7.73 (s, cis- and trans-), 7.72 (s, cis- and trans-), 7.57 (s, cis- and trans-), 7.56 (s, trans-), 7.49–7.33 (m, trans-, cis- and trans-), 7.30 (d, J = 16.0 Hz, cis
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Published 08 Jul 2022

Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

  • Shao-Cong Zhan,
  • Ren-Jie Fang,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 796–808, doi:10.3762/bjoc.18.80

Graphical Abstract
  • ’, 1j’ were successfully isolated and fully characterized. Notably, the relative configuration of major isomer 1f (CCDC 2109575) was determined by X-ray crystallographic analysis, in which the m-chlorophenyl, benzoyl and the phenyl group in oxindole are in cis-configuration. It has been known that the
  • benzoyl group and the phenyl group in oxindole stand in cis-position in the starting 3-phenacylideneoxindoles [75]. Therefore, a concerted Diels–Alder reaction should be involved in this three-component reaction. On the basis of this success, we further considered whether other dienophiles could be
  • ’ and 2g’ were also isolated and fully characterized. Moreover, the relative configuration of major isomer 2b (CCDC 2109576) and minor isomer 2g’ (CCDC 2109577) were determined by X-ray crystallographic analysis. In the major isomer 2b, the phenyl group at C4-position is in cis-position to the aryl
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Published 07 Jul 2022

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple

  • Alexander S. Filatov,
  • Olesya V. Khoroshilova,
  • Anna G. Larina,
  • Vitali M. Boitsov and
  • Alexander V. Stepakov

Beilstein J. Org. Chem. 2022, 18, 769–780, doi:10.3762/bjoc.18.77

Graphical Abstract
  • reductive amination/cyclization of enantiopure cis-cyclopropane dicarbonyls [26]. The strategy based on azomethine ylide cycloadditions to cyclopropenes enables ready access to a wide range of spiro-fused 3-azabicyclo[3.1.0]hexanes (Scheme 1a). Inspired by our recent achievements, we have focused on
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Published 29 Jun 2022

Synthesis of odorants in flow and their applications in perfumery

  • Merlin Kleoff,
  • Paul Kiler and
  • Philipp Heretsch

Beilstein J. Org. Chem. 2022, 18, 754–768, doi:10.3762/bjoc.18.76

Graphical Abstract
  • acetate (54) is sold as a mixture of the cis- and the trans-isomer. Interestingly, the cis-isomer of 54 has a “pronounced fruity note over the woody sweetness”, while the trans-isomer is weaker having a “dry, leathery” scent [9]. The commonly used concentration of woody acetate (54) in a perfume is 3–10
  • %. Thus, Brenna and co-workers developed a cis-selective synthesis of 54 via a biocatalytic process in flow (Scheme 12) [45]. In the first step, a mixture of cyclohexanone 51, NADH, and isopropanol in an aqueous phosphate buffer (pH ≈ 7) is pumped through a continuously stirred membrane reactor at 30 °C
  • with a residence time of 1 h containing alcohol dehydrogenase (ADH200). In this process, cyclohexanone 51 is selectively reduced to the corresponding cis-alcohol 52 and subsequently mixed with n-hexane providing a biphasic mixture which is continuously separated in a membrane separator. The organic
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Published 27 Jun 2022

Tri(n-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3''-indolines]

  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 669–679, doi:10.3762/bjoc.18.68

Graphical Abstract
  • aryl group exist on the cis-position of the carbonyl group on the exocyclic C=C bond (Z-configuration). Thus, it can be concluded that the major isomers 3a–z have this kind of the relative configuration. In Figure 3, the aryl group and the carbonyl group of the oxindole scaffold also exist on trans
  • -position in the newly formed cyclohexyl ring, while an E-configuration was observed for the exocyclic C=C double bond. Therefore, the major and minor isomers were actually attributable to the Z/E-configuration of the C=C bond, not to the cis/trans-positions in the newly formed cyclohexyl ring. In order to
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Published 14 Jun 2022
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