Chemoenzymatic synthesis of chiral substituted acrylate and acrylonitrile precursors for the synthesis of 3-deoxy-2-ulosonic acids and α-methylene-γ-lactones

被引：16

作者：

Crestia, D ^{[1
]}

Guérard, C ^{[1
]}

Veschambre, H ^{[1
]}

Hecquet, L ^{[1
]}

Demuynck, C ^{[1
]}

Bolte, J ^{[1
]}

机构：

[1] Univ Blaise Pascal, Lab Synth Electrosynth & Etud Syst Interet Biol, CNRS, UMR 6504, F-63177 Clermont Ferrand, France

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(01)00155-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Substituted acrylonitrile and ethyl acrylate bearing a masked alpha -hydroxyaldehyde were easily synthesised by a Barbier type reaction between the monoacetal of glyoxal and bromomethyl acrylonitrile or ethyl bromomethyl acrylate. We prepared these interesting synthons in an enantiomerically pure form by enzymatic resolution with Candida rugosa lipase. or by microbial reduction of the corresponding ketones using Aspergillus niger and Lactobacillus kefir. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：869 / 876

页数：8

共 26 条

[1]

[Anonymous], METHODS ENZYMATIC AN

[2] Microbiological reductions of chromen-4-one derivatives [J].

Besse, P ;

Baziard-Mouysset, G ;

Boubekeur, K ;

Palvadeau, P ;

Veschambre, H ;

Payard, M ;

Mousset, G .

TETRAHEDRON-ASYMMETRY, 1999, 10 (24) :4745-4754

[3]

CHAN TH, 1995, J ORG CHEM, V60, P4232

[4]

CORNIL B, 1996, APPL HOMOGENEOUS CAT, P782

[5] Rabbit muscle aldolase (RAMA) as a catalyst in a new approach for the synthesis of 3-deoxy-D-manno-2-octulosonic acid and analogues [J].

Crestia, D ;

Guérard, C ;

Bolte, J ;

Demuynck, C .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 11 (4-6) :207-212

[6] Chain extension of aldonolactones by samarium iodide mediated Dreiding-Schmidt reactions and samarium assisted Imamoto reactions [J].

Csuk, R ;

Horing, U ;

Schaade, M .

TETRAHEDRON, 1996, 52 (29) :9759-9776

[7] A STRUCTURAL BASIS FOR THE CHIRAL PREFERENCES OF LIPASES [J].

CYGLER, M ;

GROCHULSKI, P ;

KAZLAUSKAS, RJ ;

SCHRAG, JD ;

BOUTHILLIER, F ;

RUBIN, B ;

SERREQI, AN ;

GUPTA, AK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3180-3186

[8] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[9] Synthetic studies on natural products, part V - Chemical and biochemical modifications of parthenin [J].

Das, B ;

Venkataiah, B ;

Kashinatham, A .

TETRAHEDRON, 1999, 55 (21) :6585-6594

[10] PREPARATION OF OPTICALLY PURE L-2-HYDROXYALDEHYDES WITH YEAST TRANSKETOLASE [J].

EFFENBERGER, F ;

NULL, V ;

ZIEGLER, T .

TETRAHEDRON LETTERS, 1992, 33 (36) :5157-5160

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