ENANTIOMERICALLY ENRICHED ALPHA-VINYL AMINO-ACIDS VIA LIPASE-MEDIATED REVERSE TRANSESTERIFICATION

被引：28

作者：

BERKOWITZ, DB

PUMPHREY, JA

SHEN, QR

机构：

[1] Department of Chemistry, University of Nebraska-Lincoln, Lincoln

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(00)78486-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reduction of protected alpha-vinyl amino acids produces ''neopentyl'' alcohols that may be enriched in the L-antipode by lipase-mediated acylation with vinyl acetate. Subsequent deacetylation, oxidation and hydrolysis yields enantiomerically enriched L-alpha-vinyl amino acids.

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收藏

页码：8743 / 8746

页数：4

相关论文

共 20 条

[1] L-VINYLGLYCINE [J].

AFZALIARDAKANI, A ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (24) :4817-4820

[2] VERSATILE STEREOSELECTIVE SYNTHESIS OF COMPLETELY PROTECTED TRIFUNCTIONAL ALPHA-METHYLATED ALPHA-AMINO-ACIDS STARTING FROM ALANINE [J].

ALTMANN, E ;

NEBEL, K ;

MUTTER, M .

HELVETICA CHIMICA ACTA, 1991, 74 (04) :800-806

[3] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].

BAL, BS ;

CHILDERS, WE ;

PINNICK, HW .

TETRAHEDRON, 1981, 37 (11) :2091-2096

[4] THE FREE-RADICAL CHEMISTRY OF CARBOXYLIC ESTERS OF 2-SELENOPYRIDINE-N-OXIDE - A CONVENIENT SYNTHESIS OF (L)-VINYLGLYCINE [J].

BARTON, DHR ;

CRICH, D ;

HERVE, Y ;

POTIER, P ;

THIERRY, J .

TETRAHEDRON, 1985, 41 (19) :4347-4357

[5]

BERKOWITZ DB, UNPUB

[6] ASYMMETRIC-SYNTHESIS OF ALPHA-ALKYL-ALPHA-AMINO ACIDS FROM CHROMIUM CARBENE-COMPLEX-DERIVED BETA-LACTAMS [J].

COLSON, PJ ;

HEGEDUS, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5918-5924

[7] PYRIDINIUM DICHROMATE OXIDATION - MODIFICATIONS ENHANCING ITS SYNTHETIC UTILITY [J].

CZERNECKI, S ;

GEORGOULIS, C ;

STEVENS, CL ;

VIJAYAKUMARAN, K .

TETRAHEDRON LETTERS, 1985, 26 (14) :1699-1702

[8] ALPHA-ETHYNYL AND ALPHA-VINYL ANALOGS OF ORNITHINE AS ENZYME-ACTIVATED INHIBITORS OF MAMMALIAN ORNITHINE DECARBOXYLASE [J].

DANZIN, C ;

CASARA, P ;

CLAVERIE, N ;

METCALF, BW .

JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (01) :16-20

[9] A NOVEL AND EFFICIENT SYNTHESIS OF L-VINYLGLYCINE [J].

HANESSIAN, S ;

SAHOO, SP .

TETRAHEDRON LETTERS, 1984, 25 (14) :1425-1428

[10]

Maycock AL, 1979, DEV BIOCHEM, V6, P115