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Search for "aldol reaction" in Full Text gives 125 result(s) in Beilstein Journal of Organic Chemistry.

New α- and β-cyclodextrin derivatives with cinchona alkaloids used in asymmetric organocatalytic reactions

  • Iveta Chena Tichá,
  • Simona Hybelbauerová and
  • Jindřich Jindřich

Beilstein J. Org. Chem. 2019, 15, 830–839, doi:10.3762/bjoc.15.80

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  • as the promoter (not in a catalytic amount) of a Henry reaction and obtained the product with 99% ee. Subsequently, Doyagüez et al. [17] attached L-proline to β-CD via different linkers (including a triazole linker) and used the resulting organocatalysts in an aldol reaction in water, albeit with a
  • lower enantiomeric excess (54% ee). Conversely, Shen et al. [18] performed an aldol reaction in a buffer using L- and D-proline-derived CDs connected through a pyrrolidine skeleton as catalysts and observed 94% ee. More recently, Liu et al. [19] reported the excellent enantioselectivity of 99% ee in an
  • aldol reaction catalyzed by β-CD with L-proline attached through a urea moiety. Therefore, mainly proline-derived CDs have been previously tested as organocatalysts and mainly in aldol-type reactions. The limited number of functional groups attached to CD comprising mainly L-proline restricts the
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Published 01 Apr 2019

Mechanistic studies of an L-proline-catalyzed pyridazine formation involving a Diels–Alder reaction with inverse electron demand

  • Anne Schnell,
  • J. Alexander Willms,
  • S. Nozinovic and
  • Marianne Engeser

Beilstein J. Org. Chem. 2019, 15, 30–43, doi:10.3762/bjoc.15.3

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  • -proline-catalyzed aldol reaction. Organocatalysis has become a major research field with many applications and has proven to be a valuable complementary approach to organometallic or enzymatic catalysis [29][30][31][32][33][34]. The advantages especially in comparison to organometallic catalysis lie in a
  • inexpensive and easily available. The work of List and Barbas in 2000 was groundbreaking for L-proline-catalyzed reactions [40]. They published a L-proline-catalyzed asymmetric aldol reaction and suggested that the essential catalytic step is the enamine formation between the secondary amine function of L
  • aldol reaction [17]. In our case, it unfortunately does not accumulate in sufficient amounts for detection. Thus, the reaction was setup differently: instead of premixing L-proline (0.05 equiv) and tetrazine substrate 2 (1 equiv) in solution and then adding acetone (4 equiv) to start the reaction as
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Published 03 Jan 2019

Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

  • Pierre-Antoine Nocquet,
  • Aurélie Macé,
  • Frédéric Legros,
  • Jacques Lebreton,
  • Gilles Dujardin,
  • Sylvain Collet,
  • Arnaud Martel,
  • Bertrand Carboni and
  • François Carreaux

Beilstein J. Org. Chem. 2018, 14, 2949–2955, doi:10.3762/bjoc.14.274

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  • derivatives, from the same source of chirality. Results and Discussion Synthesis of vancosamine and saccharosamine glycals. The chiral (−)-lactic methyl ester was identified as the privileged starting material considering that the Evans aldol reaction via boron enolates [26][27][28] with an appropriately O
  • -protected aldehyde should afford the desired aldol adduct with a syn relative configuration between the two newly created chiral centers [29][30]. Moreover, the boron-mediated stereoselective aldol reaction is all the more interesting for our synthetic plan as stereochemical diversity can be generated
  • strategy based on an Evans’ aldol reaction. Mildly oxidizing conditions using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) were used for the removal of the p-methoxybenzyl (PMB) group to provide alcohols 14 (Scheme 3). Several palladium(II) catalysts have been tested for the conversion of alcohols to
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Published 29 Nov 2018

Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source

  • Tetsuaki Fujihara and
  • Yasushi Tsuji

Beilstein J. Org. Chem. 2018, 14, 2435–2460, doi:10.3762/bjoc.14.221

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  • amount of reductant, as exemplified by the reductive aldol reaction of α,β-unsaturated nitriles catalyzed by cobalt using phenylsilane as the reductant [34]. Yamada found that the reductive carboxylation of α,β-unsaturated compounds with CO2 proceeded in the presence of Co catalysts and reductants
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Published 19 Sep 2018

Recent applications of chiral calixarenes in asymmetric catalysis

  • Mustafa Durmaz,
  • Erkan Halay and
  • Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

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  • results clearly confirmed the cooperative effect and special role of the calixarene backbone. Aldol reaction Since chiral substituents and binding sites attached to the upper rim of the calixarene backbone can offer the full advantage of the unique inclusion properties of hydrophobic cavity, Wang et al
  • prolinamide units located appropriate array on calixarene in the presence of 2 mol % of PhCOOH catalyzed the aldol reaction in excellent yield and high enantioselectivity. Under the optimized reaction conditions, the aldol reaction of aromatic aldehydes 72 with 70 and 71 afforded the adducts in moderate to
  • respectively have been designed by Yilmaz et al. as shown in Figure 9 [65]. A new prolinamide derivative 92 with increased NH acidity has been synthesized from diformylcalixarene derivative 90 as shown in Scheme 24 [66]. Aldol reaction between 21 and 70 in water showed that catalyst 75 provided faster reaction
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Published 08 Jun 2018

Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides

  • Kartik Temburnikar and
  • Katherine L. Seley-Radtke

Beilstein J. Org. Chem. 2018, 14, 772–785, doi:10.3762/bjoc.14.65

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  • methods of C2' substitution that involve conversion of the C2'-OH to a ketone followed by Me or F substitution [87][88][89][90][91][92][93][94]. Using the Mukaiyama aldol reaction, Peifer obtained a C2'-substituted ribonolactone, which can then be employed in C-nucleoside synthesis [75]. This involves
  • '-substituted D-ribonolactone via Mukaiyama aldol reaction. A series of 2'-O-alkyl, alkyl, cycloalkyl and deoxy D-ribonolactone were synthesized using this method. B. Use of Hantzsch ester to obtain the β-anomer of C-nucleosides. Synthesis of carbocyclic C-nucleosides using cyclopentanone [53]. A. Nucleophlic
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Published 05 Apr 2018

Nanoreactors for green catalysis

  • M. Teresa De Martino,
  • Loai K. E. A. Abdelmohsen,
  • Floris P. J. T. Rutjes and
  • Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

Graphical Abstract
  • depicted in Figure 2, PQS (4a) has an OH moiety that allows for its linkage to the organocatalyst proline 4b. Also, PQS has a lipophilic component that acts as a reaction solvent for hydrophobic dienes. The latter feature allows aldol reactions to take place efficiently in water. The aldol reaction between
  • asymmetric aldol reaction of cyclohexanone and 4-nitrobenzaldehyde [83]. Cross-linked polymersome nanoreactors were also used to perform asymmetric cyclopropanation reactions in water [15]. These products are highly desired intermediates in the preparation of agrochemicals and pharmaceuticals [84][85][86
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Published 29 Mar 2018

Investigations towards the stereoselective organocatalyzed Michael addition of dimethyl malonate to a racemic nitroalkene: possible route to the 4-methylpregabalin core structure

  • Denisa Vargová,
  • Rastislav Baran and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2018, 14, 553–559, doi:10.3762/bjoc.14.42

Graphical Abstract
  • , reduction, nitro-aldol reaction, and dehydration (Scheme 1). Methylation of the ester 2 in the alpha position proceeded easily with LDA as a base and methyl iodide as an alkylating agent. The ester functionality was then reduced with DIBAL in dichloromethane to afford aldehyde 4 in 90% yield. A base
  • -mediated addition of nitromethane to the aldehyde 4 provided nitro alcohol 5. The somewhat lower yield (58%) of the aldol product 5 is likely caused by the reversibility of the nitro-aldol reaction. The yield of this reaction did not improve with longer time and unreacted aldehyde was still present in the
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Published 05 Mar 2018

Syn-selective silicon Mukaiyama-type aldol reactions of (pentafluoro-λ6-sulfanyl)acetic acid esters with aldehydes

  • Anna-Lena Dreier,
  • Andrej V. Matsnev,
  • Joseph S. Thrasher and
  • Günter Haufe

Beilstein J. Org. Chem. 2018, 14, 373–380, doi:10.3762/bjoc.14.25

Graphical Abstract
  • . The selectivity of these reactions depends on the geometry of the intermediate enolates. Here, we have reacted octyl pentafluoro-λ6-sulfanylacetate with substituted benzaldehydes and acetaldehyde under the conditions of the silicon-mediated Mukaiyama aldol reaction. The transformations proceeded with
  • : aldol reaction; ester enolate; fluorine; SF5 compounds; stereochemistry; Introduction The classical acid- or base-catalyzed directed cross aldol reaction of an aldehyde and an enolizable second carbonyl compound is one of the most powerful and reliable carbon–carbon bond-forming transformations in
  • chose the reaction of the less volatile octyl 2-(pentafluoro-λ6-sulfanyl)acetate (1) with p-nitrobenzaldehyde. Analogously to a protocol used by Ishihara et al. [35] for an Evans aldol reaction of trifluoropropanoic amides, we refluxed 1 equiv of ester 1 with 1.5 equiv trimethylsilyl
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Published 08 Feb 2018

Recent developments in the asymmetric Reformatsky-type reaction

  • Hélène Pellissier

Beilstein J. Org. Chem. 2018, 14, 325–344, doi:10.3762/bjoc.14.21

Graphical Abstract
  • than the aldol reaction, especially in the case of heterogeneous conditions. Moreover, another limitation of the Reformatsky reaction is the requirement of an α-halogen in the Reformatsky reagent. Anyway, the Reformatsky reaction is versatile since it can occur through either intra- or intermolecular
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Published 02 Feb 2018

The use of 4,4,4-trifluorothreonine to stabilize extended peptide structures and mimic β-strands

  • Yaochun Xu,
  • Isabelle Correia,
  • Tap Ha-Duong,
  • Nadjib Kihal,
  • Jean-Louis Soulier,
  • Julia Kaffy,
  • Benoît Crousse,
  • Olivier Lequin and
  • Sandrine Ongeri

Beilstein J. Org. Chem. 2017, 13, 2842–2853, doi:10.3762/bjoc.13.276

Graphical Abstract
  • followed a general procedure to access to (2S,3S)-CF3-threonine through an aldol reaction of CF3CHO with the Ni(II) complex of the chiral Schiff base of glycine which was introduced by Belokon et al. [23][24]. The chiral auxiliary (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide (11) was obtained
  • conditions gave the nickel Schiff base complex 12 in 71% yield as red crystals. The nucleophilic glycine equivalent 12 went through the aldol reaction with trifluoroacetaldehyde to give complex 13 in moderate yield (66%). Further hydrolysis of complex 13 led to the recovery of the chiral auxiliary 11 and
  • obtained through the aldol reaction of trifluoroacetaldehyde with the Ni(II) complex of the chiral Schiff base of glycine. The conformational analysis of these pentapeptides was conducted by the combined use of NMR spectroscopy and molecular dynamics simulations. NMR conformational studies showed that the
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Published 21 Dec 2017

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

  • Myriam Drouin and
  • Jean-François Paquin

Beilstein J. Org. Chem. 2017, 13, 2637–2658, doi:10.3762/bjoc.13.262

Graphical Abstract
  • protection. Xaa-ψ[CF=C]-Pro The first asymmetric synthesis of Xaa-ψ[CF=C]-Pro was reported in 2012 by Chang’s group with the synthesis of MeOCO-Val-ψ[(Z)-CF=C]-Pro 93 (Scheme 18) [52]. Their synthesis started with a stereoselective aldol reaction using (L)-threonine to furnish a chiral β-hydroxy
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Published 12 Dec 2017

Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds

  • Alexey Yu. Dubovtsev,
  • Maksim V. Dmitriev,
  • Аndrey N. Maslivets and
  • Michael Rubin

Beilstein J. Org. Chem. 2017, 13, 2179–2185, doi:10.3762/bjoc.13.218

Graphical Abstract
  • , bridged 1,3-oxazepine products 12 were formed in marginal yields, resulting from an initial aldol reaction involving the carbonyl group at C-3 of pyrroledione 9 and a subsequent intramolecular 6-endo-trig O-nucleophilic attack of the enol species at a conjugate unsaturated ketone moiety in the five
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Published 19 Oct 2017

Mechanochemical synthesis of small organic molecules

  • Tapas Kumar Achar,
  • Anima Bose and
  • Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

Graphical Abstract
  • ]. In this section some of the most important C–C bond forming reactions and their advantages are discussed. Aldol reaction In 2000, Raston and Scott first reported the aldol condensation reaction using veratraldehyde, 4-phenylcyclohexanone and 1-indanone in the presence of NaOH in a vibrating ball mill
  • -free conditions were performed using a combination of (S)-binam-L-Pro (A, 5 mol %) and benzoic acid (10 mol %) as organocatalyst [49]. Juaristi and co-workers investigated the mechanistic aspects of α,α-dipeptide derivatives of a (S)-proline- (A′)-catalyzed asymmetric aldol reaction (Scheme 2b) under
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Published 11 Sep 2017

Solvent-free sonochemistry: Sonochemical organic synthesis in the absence of a liquid medium

  • Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 1850–1856, doi:10.3762/bjoc.13.179

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  • ninhydrin and dimedone. Both systems were investigated in the complete absence of solvent and without the presence of any grinding media (such as inert silica beads) to help mediate the reaction. The aldol reaction was successfully carried out by twin screw extrusion, as I have reported previously [6]. The
  • ultrasonic irradiation at room temperature that is instigating and accelerating this chemical reaction. Further confirmation that sonochemistry is a viable method to carry out solid state organic synthesis was obtained by carrying out an aldol reaction between ninhydrin and dimedone (Scheme 2). The optimised
  • . Reaction mixture before and after ultrasonic irradiation for 60 minutes. 1H NMR spectrum of diimine 1 in CDCl3/EtOD. 1H NMR spectrum of 1,3-indandione 2 in DMSO-d6. Reaction between o-vanillin and 1,2-phenylenediamine by ultrasonic irradiation for 60 minutes. Aldol reaction between ninhydrin and dimedone
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Published 04 Sep 2017

NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones

  • Ken Takaki,
  • Makoto Hino,
  • Akira Ohno,
  • Kimihiro Komeyama,
  • Hiroto Yoshida and
  • Hiroshi Fukuoka

Beilstein J. Org. Chem. 2017, 13, 1816–1822, doi:10.3762/bjoc.13.176

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  • , the reaction efficiency was much lower than that of benzil (1a) (Scheme 4). The only isolated by-product in the reaction of 5a was bicyclo[3.2.1]octanone 8 (ca. 10%), which was formed by competitive tandem Michael–aldol reaction [21]. Cycloheptane-1,2-dione (5b) and cyclododecane-1,2-dione (5c) gave
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Published 30 Aug 2017

The chemistry and biology of mycolactones

  • Matthias Gehringer and
  • Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

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Published 11 Aug 2017

Total syntheses of the archazolids: an emerging class of novel anticancer drugs

  • Stephan Scheeff and
  • Dirk Menche

Beilstein J. Org. Chem. 2017, 13, 1085–1098, doi:10.3762/bjoc.13.108

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  • a boron-mediated anti-aldol reaction [67] of lactate-derived ethyl ketone 13 with aldehyde 12, which in turn was available from aldehyde 9 by HWE olefination. This Paterson aldol reaction and related aldol reactions, which have been amply used by the Menche group [68][69][70], proceeded with
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Published 07 Jun 2017

Synthesis of D-manno-heptulose via a cascade aldol/hemiketalization reaction

  • Yan Chen,
  • Xiaoman Wang,
  • Junchang Wang and
  • You Yang

Beilstein J. Org. Chem. 2017, 13, 795–799, doi:10.3762/bjoc.13.79

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  • aldol/hemiketalization reaction of a C4 aldehyde with a C3 ketone provides the differentially protected ketoheptose building block, which can be further reacted to furnish target D-manno-heptulose. Keywords: aldol reaction; cascade reaction; D-manno-heptulose; higher-carbon sugar; ketoheptose
  • chain elongations of aldoses employing the Henry reaction, the aldol reaction, and the Wittig reaction for the preparation of ketoheptoses [20][21][22], sugar lactones were also often utilized for the synthesis of D-manno-heptulose via reactions with C-nucleophiles or conversion into exocyclic glycals
  • on TLC monitoring. Given that the C4 aldehyde 3 was unstable upon purification by silica gel column chromatography, it was immediately used for the subsequent coupling after the extraction procedure. The aldol reaction of aldehyde 3 with the readily available ketone 4 [42][43] under the catalysis of
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Published 28 Apr 2017

Formose reaction controlled by boronic acid compounds

  • Toru Imai,
  • Tomohiro Michitaka and
  • Akihito Hashidzume

Beilstein J. Org. Chem. 2016, 12, 2668–2672, doi:10.3762/bjoc.12.263

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  • formose reaction consists of several elemental reaction steps, e.g., acyloin condensation, aldol reaction, retro-aldol reaction, aldose–ketose isomerization, and Cannizzaro reaction, and the product, formose, is a complicated mixture of more than thirty species of sugars and sugar alcohols including non
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Published 08 Dec 2016

Formose reaction accelerated in aerosol-OT reverse micelles

  • Makoto Masaoka,
  • Tomohiro Michitaka and
  • Akihito Hashidzume

Beilstein J. Org. Chem. 2016, 12, 2663–2667, doi:10.3762/bjoc.12.262

Graphical Abstract
  • rate-determining step of the formose reaction. It is known that glycolaldehyde acts as a cocatalyst. Thus, when the concentration of glycolaldehyde reaches a certain level, formaldehyde is consumed rapidly to form a complicated mixture of sugars predominantly via aldol reaction and aldose–ketose
  • transformation in the sugar formation period. When formaldehyde is consumed quantitatively, the reaction mixture turns yellow. In the sugar degradation period, the sugars formed are decomposed dominantly through cross-Cannizzaro reaction and retro-aldol reaction to form a more complicated reaction mixture. The
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Published 07 Dec 2016

Towards the development of continuous, organocatalytic, and stereoselective reactions in deep eutectic solvents

  • Davide Brenna,
  • Elisabetta Massolo,
  • Alessandra Puglisi,
  • Sergio Rossi,
  • Giuseppe Celentano,
  • Maurizio Benaglia and
  • Vito Capriati

Beilstein J. Org. Chem. 2016, 12, 2620–2626, doi:10.3762/bjoc.12.258

Graphical Abstract
  • . Keywords: continuous process; DES; organocatalysis; proline; stereoselective aldol reaction; Introduction The aldol reaction is a powerful synthetic tool to create new C–C bonds [1]. It offers several possibilities to control the stereochemical outcome of the process and to afford stereochemically defined
  • chiral products [2]. Among all the possible options, the L-proline-catalysed stereoselective cross-aldol reaction remains the greener choice. After the pioneering works by List and Barbas [3], a huge effort was made by the scientific community to improve both the yield and the stereoselectivity of the
  • eutectic mixtures as reaction media (Table 1) [40]. The behaviour of DES mixtures A–E in the proline-catalysed model aldol reaction between cyclohexanone and 4-nitrobenzaldehyde was preliminarily investigated under standard batch conditions (Scheme 1). In our hands, the reaction proceeded completely in 20
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Published 05 Dec 2016

Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-addition/aldol reaction followed by RCM/syn-dihydroxylation

  • Michał Malik and
  • Sławomir Jarosz

Beilstein J. Org. Chem. 2016, 12, 2602–2608, doi:10.3762/bjoc.12.255

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  • 1,4-addition of vinylmagnesium bromide to sugar-derived cyclohexenone, followed by an aldol reaction with a derivative of but-3-enal. The obtained diene is then subjected to an assisted tandem catalytic sequence: ring-closing metathesis with the subsequent reuse of the Ru-catalyst in the syn
  • possibility of using a copper-catalyzed one-pot 1,4-addition of vinylmagnesium bromide to sugar-derived cyclic α,β-unsaturated ketones (such as 9), followed by an aldol reaction with an optically pure derivative of but-2-enal 10 to obtain a mixture of diastereomeric dienes, such as 11 (Scheme 2). As a result
  • of this transformation, three new stereogenic centers are generated. A copper-catalyzed 1,4-addition of organometallic reagents to cyclic α,β-unsaturated ketones, followed by an aldol reaction has been already used in the synthesis of complex natural products [26][27][28][29][30][31][32][33
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Published 01 Dec 2016

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

  • Darcy J. Atkinson,
  • Briar J. Naysmith,
  • Daniel P. Furkert and
  • Margaret A. Brimble

Beilstein J. Org. Chem. 2016, 12, 2325–2342, doi:10.3762/bjoc.12.226

Graphical Abstract
  • synthetically broken down into tripeptides 78 and 79 (Scheme 15). Tripeptide 78 was further disconnected into protected serine 80 and protected β-hydroxyenduracididine residues 81 and 82. The synthesis of key amino acids 81 and 82 was based on an aldol reaction between protected aldehyde 83 and glycine 84
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Published 07 Nov 2016

A chiral analog of the bicyclic guanidine TBD: synthesis, structure and Brønsted base catalysis

  • Mariano Goldberg,
  • Denis Sartakov,
  • Jan W. Bats,
  • Michael Bolte and
  • Michael W. Göbel

Beilstein J. Org. Chem. 2016, 12, 1870–1876, doi:10.3762/bjoc.12.176

Graphical Abstract
  • base the retro-aldol reaction of some cycloadducts with kinetic resolution of the enantiomers. In three cases, the retro-aldol products (48–83% ee) could be recrystallized to high enantiopurity (≥95% ee). The absolute configuration of several compounds is supported by anomalous X-ray diffraction and by
  • base-catalyzed retro-aldol reaction and they are not converted backwards into Diels–Alder adducts under such conditions [19][25][26]. Our results shown below give further support to this view. Riant, Kagan and Ricard have demonstrated for the first time that deprotonated anthrones may coordinate to
  • moderate stereoselectivity is superimposed with a kinetic resolution of enantiomers in the subsequent retro-aldol reaction. Both are catalyzed by the chiral guanidine 10. As a result, the numbers shown in Table 1 are not constant but depend on the relative turnover of each reaction. When rac-25 reacted
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Published 19 Aug 2016
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