A NOVEL CHIRAL BUILDING-BLOCK WITH NEOPENTANE FRAMEWORK FOR SYNTHESIS - CHEMOENZYMATIC PREPARATION OF (R)-CH3C(CH2OSO2CF3)(CH2CL)(CH2BR)

被引：17
|
作者：
HEIDEL, H
HUTTNER, G
VOGEL, R
HELMCHEN, G
机构：
[1] UNIV HEIDELBERG,INST ANORGAN CHEM,D-69120 HEIDELBERG,GERMANY
[2] UNIV HEIDELBERG,INST ORGAN CHEM,D-69120 HEIDELBERG,GERMANY
来源：
CHEMISCHE BERICHTE | 1994年 / 127卷 / 01期
关键词：
PIG LIVER ESTERASE; ENANTIOSELECTIVE HYDROLYSIS; ASYMMETRIZED NEOPENTANE; REACTIVE CHIRAL BUILDING BLOCK;
D O I：
10.1002/cber.19941270138
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The pig liver esterase (PLE) catalysed hydrolysis of the prochiral malonic ester (BzlOCH(2)) (Me)C(COOMe)(2) (1) leads to its chiral monoester 2 in selectivities up to 81% ee. Compound 2 is an ideal entry point for the enantioselective synthesis of 1,1',1''-substituted neopentanes CH3C(CH(2)X)- (CH2Y)(CH(2)Z) with three different leaving groups, X, Y, and Z. CH3C(CH2OSO2CF3)(CH2Br) (CH2Cl) (8) is a versatile reactive building block for the asymmetric synthesis of compounds containing the neopentane-C-5 skeleton.
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页码：271 / 274
页数：4
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