Search results

Search for "allylic alcohols" in Full Text gives 87 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of a sucrose dimer with enone tether; a study on its functionalization

  • Zbigniew Pakulski,
  • Norbert Gajda,
  • Magdalena Jawiczuk,
  • Jadwiga Frelek,
  • Piotr Cmoch and
  • Sławomir Jarosz

Beilstein J. Org. Chem. 2014, 10, 1246–1254, doi:10.3762/bjoc.10.124

Graphical Abstract
  • selective and provides the corresponding allylic alcohols with the R configuration at the newly created stereogenic center, as the only products. This can be rationalized assuming the cyclic model of such reduction [25] shown in Scheme 2. We expected, therefore, also very high selectivity in the reduction
PDF
Album
Supp Info
Full Research Paper
Published 28 May 2014

A unified approach to the important protein kinase inhibitor balanol and a proposed analogue

  • Tapan Saha,
  • Ratnava Maitra and
  • Shital K. Chattopadhyay

Beilstein J. Org. Chem. 2013, 9, 2910–2915, doi:10.3762/bjoc.9.327

Graphical Abstract
  • primary alcohol 20 was oxidized carefully under modified Swern conditions [63] to provide the α-chiral aldehyde 21 which was used directly in the next step. Addition of vinylmagnesium bromide to aldehyde 21 under optimized conditions gave a separable mixture of the allylic alcohols 22 and 23 in a combined
PDF
Album
Supp Info
Full Research Paper
Published 19 Dec 2013

Novel supramolecular affinity materials based on (−)-isosteviol as molecular templates

  • Christina Lohoelter,
  • Malte Brutschy,
  • Daniel Lubczyk and
  • Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2013, 9, 2821–2833, doi:10.3762/bjoc.9.317

Graphical Abstract
  • ester substituent, the detour via protecting groups in the synthesis of alkylated triptycene 17 was subsequently avoided. Therefore, alkylated diketone 18 was synthesized, starting from (−)-isosteviol (Scheme 8). Since alkenes are known to participate in Riley oxidations as well, rendering allylic
  • alcohols, there is only one route to 18. After Riley oxidation of 1, alkylation was carried out under the same reaction conditions as before, providing the desired product in a yield of 85% [70]. 18 was then brought to reaction with hexaammoniumtriptycene hexachloride 4 (Scheme 9). The corresponding all
PDF
Album
Supp Info
Full Research Paper
Published 09 Dec 2013

Stereoselectively fluorinated N-heterocycles: a brief survey

  • Xiang-Guo Hu and
  • Luke Hunter

Beilstein J. Org. Chem. 2013, 9, 2696–2708, doi:10.3762/bjoc.9.306

Graphical Abstract
  • architectures. For example, 45 can react selectively with primary and allylic alcohols in the presence of secondary and tertiary alcohols, and the reaction will also tolerate the presence of carbonyl groups [57]. Some N-heterocyclic targets that have been synthesised in one step using 45 as the
PDF
Album
Review
Published 29 Nov 2013

Garner’s aldehyde as a versatile intermediate in the synthesis of enantiopure natural products

  • Mikko Passiniemi and
  • Ari M.P. Koskinen

Beilstein J. Org. Chem. 2013, 9, 2641–2659, doi:10.3762/bjoc.9.300

Graphical Abstract
  • anti-selectivities were achieved (up to 17:1 anti/syn). Without additives the reaction gave a 4:1 anti/syn mixture of allylic alcohols 62 and 63. Chelating metals gave rise to the syn-adduct 63. When we used ZnCl2 dissolved in Et2O as the chelating agent, the syn-selectivity rose to about 1:6 favouring
PDF
Album
Review
Published 26 Nov 2013

New developments in gold-catalyzed manipulation of inactivated alkenes

  • Michel Chiarucci and
  • Marco Bandini

Beilstein J. Org. Chem. 2013, 9, 2586–2614, doi:10.3762/bjoc.9.294

Graphical Abstract
  • respect to different π-systems. In particular, the intrinsic inertness of alkylgold intermediate 1 (i.e. Csp3–Au bond) towards protodeauration (path a, Figure 2) determines the scarce reactivity of alkenes in nucleophilic addition reactions [6]. The use of allylic alcohols as C=C surrogates opens up an
  • ][13]. In this review some selected examples of gold-catalyzed nucleophilic additions to inactivated alkenes will be discussed with particular emphasis on the corresponding reaction machinery. In the context of this review, allylic alcohols will be treated as inactivated olefins, considering that
  • -based electrophilc activation of the C=C, with consequent nucleophilic attack by the ylidic carbon onto the internal carbon of the double bond. Finally, the intermediate lactone 92 underwent cyclopropanation, delivering SPh2 as a leaving group (Scheme 24b). 5 Addition to allylic alcohols The use of
PDF
Album
Review
Published 21 Nov 2013
Graphical Abstract
  • of its diastereomers, and help to resolve the remaining structural ambiguities, i.e. the absolute configurations at C4, C5 and C6. Based on the transition-state model for the Sharpless epoxidation of allylic alcohols bearing a stereogenic centre in the allylic position [64], we expected that
PDF
Album
Supp Info
Full Research Paper
Published 18 Nov 2013

Regioselective carbon–carbon bond formation of 5,5,5-trifluoro-1-phenylpent-3-en-1-yne

  • Motoki Naka,
  • Tomoko Kawasaki-Takasuka and
  • Takashi Yamazaki

Beilstein J. Org. Chem. 2013, 9, 2182–2188, doi:10.3762/bjoc.9.256

Graphical Abstract
  • ] towards MeLi, where the proportion of two possible products, propargylic alcohols 2 and allylic alcohols 3, was proved to be significantly dependent on the equivalents of MeLi used. Thus, as shown in Scheme 1, under the action of up to 1.6 equiv of MeLi, 2 was obtained as a sole product probably by
  • alkyne eventually captured appropriate aldehydes to afford CF3-containing propargylic alcohols 2 [8][9][10][11][12]. Alternatively, stereospecific and exclusive construction of the corresponding allylic alcohols 3 was attained by utilization of greater than 1.7 equiv of MeLi where the stabilized
  • nicely accepted as electrophiles. The allylic alcohols 5 were formed as the major product without exception in a similar 5/(5+6) ratio of 70–75% (Table 2, entries 1 to 5). An inseparable mixture of the compounds 5 and 6 was also synthesized from aliphatic aldehydes as shown in entries 5 and 6 in Table 2
PDF
Album
Supp Info
Full Research Paper
Published 23 Oct 2013

Gold(I)-catalysed one-pot synthesis of chromans using allylic alcohols and phenols

  • Eloi Coutant,
  • Paul C. Young,
  • Graeme Barker and
  • Ai-Lan Lee

Beilstein J. Org. Chem. 2013, 9, 1797–1806, doi:10.3762/bjoc.9.209

Graphical Abstract
  • Eloi Coutant Paul C. Young Graeme Barker Ai-Lan Lee Institute of Chemical Sciences, Heriot-Watt University, Edinburgh, EH14 1LP, United Kingdom 10.3762/bjoc.9.209 Abstract A gold(I)-catalysed reaction of allylic alcohols and phenols produces chromans regioselectively via a one-pot Friedel–Crafts
  • allylation/intramolecular hydroalkoxylation sequence. The reaction is mild, practical and tolerant of a wide variety of substituents on the phenol. Keywords: allylic alcohols; chromans; Friedel–Crafts; gold catalysis; heterocycles; Introduction Chromans (dihydrobenzopyrans) are important and ubiquitous
  • allylated phenol intermediate (via hydroalkoxylation). Initially, traditional allylating reagents such as allylic acetates were employed in Friedel–Crafts allylations [14], but more recently, there has been a distinct drive towards utilising more environmentally benign allylic alcohols (via a direct
PDF
Album
Supp Info
Full Research Paper
Published 04 Sep 2013

Re2O7-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles

  • Wantanee Sittiwong,
  • Michael W. Richardson,
  • Charles E. Schiaffo,
  • Thomas J. Fisher and
  • Patrick H. Dussault

Beilstein J. Org. Chem. 2013, 9, 1526–1532, doi:10.3762/bjoc.9.174

Graphical Abstract
  • Brønsted or Lewis acid, or by conversion to an activated intermediate such as a haloacetal [1]. Perrhenates, best known as catalysts for large-scale alkene metathesis [2] and isomerization of allylic alcohols [3][4][5][6][7][8][9][10], have been shown to promote condensation of carbonyls with hydrogen
  • peroxide or hydroperoxides [11][12], intramolecular displacements of reversibly formed hemiacetals and allylic alcohols [8][13], displacement of resonance-activated alcohols with electron-poor nitrogen nucleophiles [14], and a synthesis of homoallylated amines from condensation of carbonyl groups with an
PDF
Album
Supp Info
Full Research Paper
Published 30 Jul 2013

Hypervalent iodine/TEMPO-mediated oxidation in flow systems: a fast and efficient protocol for alcohol oxidation

  • Nida Ambreen,
  • Ravi Kumar and
  • Thomas Wirth

Beilstein J. Org. Chem. 2013, 9, 1437–1442, doi:10.3762/bjoc.9.162

Graphical Abstract
  • Nida Ambreen Ravi Kumar Thomas Wirth Cardiff University, School of Chemistry, Park Place, Cardiff CF10 3AT, UK 10.3762/bjoc.9.162 Abstract Hypervalent iodine(III)/TEMPO-mediated oxidation of various aliphatic, aromatic and allylic alcohols to their corresponding carbonyl compounds was
  • experiments were performed with at least 5 mol % TEMPO catalyst. To extend the substrate scope, various benzylic, aliphatic and allylic alcohols were investigated. Good yields at short reaction times and a high selectivity towards the oxidized products were observed as shown in Table 1. Over-oxidation to the
PDF
Album
Full Research Paper
Published 17 Jul 2013

Synthesis of skeletally diverse alkaloid-like molecules: exploitation of metathesis substrates assembled from triplets of building blocks

  • Sushil K. Maurya,
  • Mark Dow,
  • Stuart Warriner and
  • Adam Nelson

Beilstein J. Org. Chem. 2013, 9, 775–785, doi:10.3762/bjoc.9.88

Graphical Abstract
  • had only been exemplified by varying pairs of unsaturated building blocks [14]. Thus, by exploiting the linker 1, which is an allyl alcohol or allyl amine equivalent, all of the products were inevitably allylic alcohols or cyclic allylic amines. Here, we demonstrate that the approach is considerably
PDF
Album
Supp Info
Full Research Paper
Published 22 Apr 2013

Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines

  • Kebin Mao,
  • Guoqin Fan,
  • Yuanhong Liu,
  • Shi Li,
  • Xu You and
  • Dan Liu

Beilstein J. Org. Chem. 2013, 9, 621–627, doi:10.3762/bjoc.9.69

Graphical Abstract
  • ], iodocyclocarbamates [19] and isoxazolines [20]. Although it has been reported that allylic amines can be synthesized by methods such as amination of allylic alcohols [21][22][23][24], direct allylic amination of simple alkenes [25][26][27], Morita–Baylis–Hillman reaction [28], alkenylation of imines [29][30][31][32
PDF
Album
Supp Info
Full Research Paper
Published 27 Mar 2013

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

  • Kei Murakami and
  • Hideki Yorimitsu

Beilstein J. Org. Chem. 2013, 9, 278–302, doi:10.3762/bjoc.9.34

Graphical Abstract
  • afford 2B or 2C (Scheme 8). Further transmetalation of vinyliron intermediate 2B or 2C with R′MgBr yielded the corresponding vinylmagnesium intermediate 2D. Therefore, selective synthesis of both regioisomers of allylic alcohols can be accomplished by simply choosing transition-metal catalysts (Cu or Fe
PDF
Album
Review
Published 11 Feb 2013

Stereoselective synthesis of tetrasubstituted alkenes via a sequential carbocupration and a new sulfur–lithium exchange

  • Andreas Unsinn,
  • Cora Dunst and
  • Paul Knochel

Beilstein J. Org. Chem. 2012, 8, 2202–2206, doi:10.3762/bjoc.8.248

Graphical Abstract
  • , −78 °C, 10 min) provides directly the Z-styryllithium 14, which stereoselectively adds to α,α,α-trifluoroacetophenone (0.8 equiv, −78 °C, 0.5 h) and cyclopentanone (0.8 equiv, −78 °C, 0.5 h) to afford the expected tertiary allylic alcohols 15a–b in 71–82% yield and E/Z ratios of >1:99. Conclusion In
PDF
Album
Supp Info
Letter
Published 18 Dec 2012

Flow photochemistry: Old light through new windows

  • Jonathan P. Knowles,
  • Luke D. Elliott and
  • Kevin I. Booker-Milburn

Beilstein J. Org. Chem. 2012, 8, 2025–2052, doi:10.3762/bjoc.8.229

Graphical Abstract
  • , despite the reactor volume being only 285 µL [39]. This output was 2.6 times that of a 50 mL batch reactor. The same reactor was also successfully applied to the oxidation of allylic alcohols for the synthesis of the antimalarial artemisinin, and the conversion of α-terpinene to ascaridole. Addition of a
PDF
Album
Review
Published 21 Nov 2012

Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine

  • David. M. Hodgson and
  • Rosanne S. D. Persaud

Beilstein J. Org. Chem. 2012, 8, 1896–1900, doi:10.3762/bjoc.8.219

Graphical Abstract
  • oxaphosphetane 3, followed by deprotonation typically using PhLi [5]. We recently reported the use of methylenetriphenylphosphorane (2) (R2 = H) in this chemistry for the synthesis of Z-allylic esters such as 6 [8] and conjugated E-allylic alcohols such as 7 [9]. β-Lithiooxyphosphonium ylides 4 (R2 = H) can also
  • terminal epoxides are readily available as single enantiomers [38][39], it was considered important to study the possibility of using an aldehyde electrophile with the epoxide-derived ylide. This would provide an entry into allylic alcohols [40], where the epoxide stereocentre is preserved in the product
PDF
Album
Supp Info
Full Research Paper
Published 07 Nov 2012

Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium

  • Michael Dobmeier,
  • Josef M. Herrmann,
  • Dieter Lenoir and
  • Burkhard König

Beilstein J. Org. Chem. 2012, 8, 330–336, doi:10.3762/bjoc.8.36

Graphical Abstract
  • (Table 1, entry 12), but some of the material was lost due to ester hydrolysis. Allylic alcohols are completely consumed, but the corresponding alkenes could not be isolated as pure products (Table 2). Mixtures of eliminiation and deoxygenation products, in some cases also rearangement of the
PDF
Album
Supp Info
Full Research Paper
Published 02 Mar 2012

Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols

  • Michel Chiarucci,
  • Mirko Locritani,
  • Gianpiero Cera and
  • Marco Bandini

Beilstein J. Org. Chem. 2011, 7, 1198–1204, doi:10.3762/bjoc.7.139

Graphical Abstract
  • tolerance make this catalytic process a promising route for the synthesis of architecturally complex polycyclic structures. Keywords: alcohol; butyrolactone; carbene; gold-catalysis; intramolecular oxaallylic alkylation; Introduction Allylic alcohols are highly desirable, readily available, cheap, and
  • activation of allylic alcohols [27][28][29][30][31] with esters [32][33][34][35][36][37]. In this direction, we targeted malonyl alcohols 1 as a readily available class of model acyclic precursors to create chemical diversity through an oxaallylic ring-closing reaction (Figure 1). It should be noted that the
  • alkylation procedure to obtain valuable precursors (i.e., lactams and lactones) of podophyllotoxin analogs [39][40]. However, to the best of our knowledge, no examples of metal-catalyzed lactonization through direct activation of allylic alcohols have been described so far. Results and Discussion At the
PDF
Album
Supp Info
Letter
Published 01 Sep 2011

Triple-channel microreactor for biphasic gas–liquid reactions: Photosensitized oxygenations

  • Ram Awatar Maurya,
  • Chan Pil Park and
  • Dong-Pyo Kim

Beilstein J. Org. Chem. 2011, 7, 1158–1163, doi:10.3762/bjoc.7.134

Graphical Abstract
  • promising for performing efficient photosensitized oxygenation of citronellol in condensed solutions that would minimize the waste of solvents. Photosensitized oxygenation of allylic alcohols The photosensitized oxygenation of allylic alcohols was taken as a second model reaction to illustrate the
PDF
Album
Supp Info
Letter
Published 24 Aug 2011

Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays

  • Ian Cumpstey,
  • Jens Frigell,
  • Elias Pershagen,
  • Tashfeen Akhtar,
  • Elena Moreno-Clavijo,
  • Inmaculada Robina,
  • Dominic S. Alonzi and
  • Terry D. Butters

Beilstein J. Org. Chem. 2011, 7, 1115–1123, doi:10.3762/bjoc.7.128

Graphical Abstract
  • pseudodisaccharides. Triflamides and nosylamides were similarly effective as nucleophiles in Mitsunobu coupling reactions with allylic alcohols. The Mitsunobu coupling reactions proceeded with inversion of configuration, and SN2’ type reactions with C=C double bond migration were not observed. A palladium catalysed
PDF
Album
Supp Info
Full Research Paper
Published 16 Aug 2011

Recent advances in the gold-catalyzed additions to C–C multiple bonds

  • He Huang,
  • Yu Zhou and
  • Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

Graphical Abstract
  • . In addition to intermolecular addition, Mukherjee and Widenhoefer recently reported a gold(I)-catalyzed intramolecular amination of allylic alcohols 130 with alkylamines (Scheme 23) [61]. 3.2 Imines as nucleophiles Gold-catalyzed cyclizations of O-propioloyl oximes via C–N bond formation followed by
  • (III) intermediate. Besides the intramolecular addition of ureas, Widenhoefer’s group reported a gold(I)-catalyzed intermolecular amination of allylic alcohols 143 with cyclic ureas 142 (Scheme 25) [67]. Gold-catalyzed reactions of ortho-alkynyl-N-sulfonylanilines 146 produced the corresponding 3
PDF
Album
Review
Published 04 Jul 2011

Gold-catalyzed propargylic substitutions: Scope and synthetic developments

  • Olivier Debleds,
  • Eric Gayon,
  • Emmanuel Vrancken and
  • Jean-Marc Campagne

Beilstein J. Org. Chem. 2011, 7, 866–877, doi:10.3762/bjoc.7.99

Graphical Abstract
  • diarylmethanol, benzylic and allylic alcohols (Scheme 9) [24][59][60][61]. This reaction was further extended to tertiary alcohols by Asensio [62]. Shortly after the publication of our seminal results [23], the direct substitution of activated (propargylic, benzylic and allylic) alcohols became of increasing
PDF
Album
Review
Published 28 Jun 2011

A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers

  • Berenger Biannic,
  • Thomas Ghebreghiorgis and
  • Aaron Aponick

Beilstein J. Org. Chem. 2011, 7, 802–807, doi:10.3762/bjoc.7.91

Graphical Abstract
  • -biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate, the cyclization reactions were complete within minutes to hours, depending on the substrate. The reaction progress was monitored by GC, and comparisons between substrates demonstrate that reactions of allylic alcohols are faster than the
  • more synthetically useful substrates. Conclusion In conclusion, it has been demonstrated that a variety of allylic ethers undergo Au-catalyzed formal SN2' reactions to form tetrahydropyrans. The reaction of allylic alcohols appears to be faster, although the leaving group is traditionally not
PDF
Album
Supp Info
Full Research Paper
Published 14 Jun 2011

Highly efficient gold(I)-catalyzed Overman rearrangement in water

  • Dong Xing and
  • Dan Yang

Beilstein J. Org. Chem. 2011, 7, 781–785, doi:10.3762/bjoc.7.88

Graphical Abstract
  • allylic trichloroacetimidates to allylic trichloroacetamides (Overman rearrangement) is a powerful and attractive strategy for the synthesis of allylic amines from readily available allylic alcohols [1][2]. This transformation can be conducted thermally at high temperatures or by transition metal
PDF
Album
Supp Info
Letter
Published 08 Jun 2011
Other Beilstein-Institut Open Science Activities