LIPASE MEDIATED RESOLUTION OF CHIRAL (E)-VINYLSILANES - AN IMPROVED PROCEDURE FOR THE PRODUCTION OF (R)-(E)-1-TRIALKYLSILYL-1-BUTEN-3-OL AND (S)-(E)-1-TRIALKYLSILYL-1-BUTEN-3-OL DERIVATIVES

被引：20

作者：

SPARKS, MA ^{[1
]}

PANEK, JS ^{[1
]}

机构：

[1] BOSTON UNIV,METCALF CTR SCI & ENGN,DEPT CHEM,BOSTON,MA 02215

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 33期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)79869-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A crude enzymic extract of Pseudomonas AK in pentane catalyzes the transesterification of chiral (E)-vinylsilanes 1, resulting in the production of highly enantiomerically enriched (R)- and (S)-(E)-1-trialkylsilyl-1-buten-3-ol derivatives (S)-2 and (R)-3. A series of related vinylsilanes and two-different lipases have been screened to identify optimal reaction conditions.

引用

页码：4085 / 4088

页数：4

共 14 条

[1] KINETIC RESOLUTIONS OF CHIRAL UNSATURATED ALCOHOLS THAT CANNOT BE RESOLVED EFFICIENTLY VIA ENANTIOSELECTIVE EPOXIDATION [J].

BURGESS, K ;

JENNINGS, LD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7434-7436

[2] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].

CHEN, CS ;

FUJIMOTO, Y ;

GIRDAUKAS, G ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299

[3] ENZYMATIC-REACTIONS IN ORGANIC-SYNTHESIS .2. ESTER INTERCHANGE OF VINYL ESTERS [J].

DEGUEILCASTAING, M ;

DEJESO, B ;

DROUILLARD, S ;

MAILLARD, B .

TETRAHEDRON LETTERS, 1987, 28 (09) :953-954

[4]

Ireland R. E., 1988, ALDRICHIM ACTA, V21, P59

[5] STEREOCHEMICAL CONTROL IN THE ESTER ENOLATE CLAISEN REARRANGEMENT .1. STEREOSELECTIVITY IN SILYL KETENE ACETAL FORMATION [J].

IRELAND, RE ;

WIPF, P ;

ARMSTRONG, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :650-657

[6] ESTER ENOLATE CLAISEN REARRANGEMENT - STEREOCHEMICAL CONTROL THROUGH STEREOSELECTIVE ENOLATE FORMATION [J].

IRELAND, RE ;

MUELLER, RH ;

WILLARD, AK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) :2868-2877

[7] THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].

KATSUKI, T ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976

[8]

KILBANOV AM, 1990, ACCOUNTS CHEM RES, V23, P114

[9] A HIGHLY EFFICIENT KINETIC RESOLUTION OF GAMMA-TRIMETHYLSILYL AND BETA-TRIMETHYLSILYL SECONDARY ALLYLIC ALCOHOLS BY THE SHARPLESS ASYMMETRIC EPOXIDATION [J].

KITANO, Y ;

MATSUMOTO, T ;

SATO, F .

TETRAHEDRON, 1988, 44 (13) :4073-4086

[10]

PANEK JS, 1990, TETRAHEDRON-ASYMMETR, V11, P801

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