DIASTEREOSELECTIVE ALDOL CONDENSATION OF DIRECTLY GENERATED TITANIUM ENOLATES OF ACTIVATED ESTERS

被引:29
作者
ANNUNZIATA, R
CINQUINI, M
COZZI, F
COZZI, PG
CONSOLANDI, E
机构
[1] UNIV MILAN,CTR CNR,VIA C GOLGI 19,I-20133 MILAN,ITALY
[2] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
关键词
D O I
10.1016/S0040-4020(01)81945-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Simply generated (TiCl4, Et3N, -78-degrees-C) titanium enolates of some thioesters and alpha-thio substituted esters undergo aldol condensations with achiral and chiral aldehydes with low to high stereoselectivity. An H-1-NMR study of the TiCl4/ester complexation and of the enolization process is presented. The relation between the enolate structure and the aldol product stereochemistry is discussed.
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页码:7897 / 7910
页数:14
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