Stereoselective alkylation-reduction of β-keto nitriles by the fungus Curvularia lunata

被引：29

作者：

Dehli, JR ^{[1
]}

Gotor, V ^{[1
]}

机构：

[1] Univ Oviedo, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(01)00269-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The alkylation-reduction (AR) reaction of beta -keto nitriles by growing cells of Curvularia lunata CECT 2130 has been explored. The reaction conditions for the ethylation of benzoylacetonitrile have been optimized in terms of both yield and stereoselectivity and the mechanism of this biotransformation vas studied. The scope of this reaction has been extended to other alkylations (R = Et, Pr, Bu, iso-Bu) and to a series of aromatic and heteroaromatic substrates, yielding the corresponding optically active alpha -alkyl beta -hydroxy nitrites. The yield (directly related to competing carbonyl reduction reaction) depends on the substrate bulk. whereas the enantiomeric and diastereomeric excesses (both up to 98%) seem to be dependent on several Factors. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1485 / 1492

页数：8

共 22 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[2]

AZERAD R, 1992, NATO ADV SCI I C-MAT, V381, P421

[3] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[4] 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

[5] Enantio- and chemoselective bioreduction of β-keto nitriles by the fungus Curvularia lunata [J].

Dehli, JR ;

Gotor, V .

TETRAHEDRON-ASYMMETRY, 2000, 11 (18) :3693-3700

[6] CHEMOENZYMATIC ALKYLATION OF ACTIVE METHYLENE-COMPOUNDS [J].

FUGANTI, C ;

PEDROCCHIFANTONI, G ;

SERVI, S .

TETRAHEDRON LETTERS, 1990, 31 (29) :4195-4198

[7] Enzymatic ammonolysis of ethyl (±)-4-chloro-3-hydroxybutanoate.: Chemoenzymatic syntheses of both enantiomers of pyrrolidin-3-ol and 5-(chloromethyl)-1,3-oxazolidin-2-one [J].

García-Urdiales, E ;

Rebolledo, F ;

Gotor, V .

TETRAHEDRON-ASYMMETRY, 1999, 10 (04) :721-726

[8]

GILCHRIST TL, 1985, HETEROCYCLIC CHEM, P160

[9] Biotransformations of benzoylacetonitrile with the fungus Curvularia lunata:: highly diastereo- and enantioselective synthesis of α-alkyl β-hydroxy nitriles and γ-amino alcohols [J].

Gotor, V ;

Dehli, JR ;

Rebolledo, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (03) :307-309

[10] A NOVEL CARBON-CARBON BOND FORMATION IN THE COURSE OF BAKERS-YEAST REDUCTION OF CYANOACETONE [J].

ITOH, T ;

TAKAGI, Y ;

FUJISAWA, T .

TETRAHEDRON LETTERS, 1989, 30 (29) :3811-3812

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