ASYMMETRIC-SYNTHESIS OF 2-CHLORO-ALKANOIC AND 2-BROMO-ALKANOIC ACIDS BY HALOGENATION OF ALPHA-D-GLUCOFURANOSE-DERIVED SILYL KETENE ACETALS

被引：13

作者：

ANGIBAUD, P

CHAUMETTE, JL

DESMURS, JR

DUHAMEL, L

PLE, G

VALNOT, JY

DUHAMEL, P

机构：

[1] UNIV ROUEN, FAC SCI, IRCOF, CNRS, URA 464, F-76821 MONT ST AIGNAN, FRANCE

[2] RHONE POULENC RECH, CRIT, F-69192 ST FONS, FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 08期

关键词：

D O I：

10.1016/0957-4166(95)00251-J

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Optically active (S)-2-bromo- and a-chloro-alkanoic acids 6 and 7 have been obtained via the diastereoselective halogenation of chiral silyl ketene acetals 3a-f, and subsequent saponificatian of the resulting crude esters. Examples characterized by e.e. values up to 95% are reported. The diastereoface selectivity is independent of the silyl ketene acetal En configuration.

引用

页码：1919 / 1932

页数：14

共 74 条

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