Highly stereoselective aldol reactions of titanium enolates from ethyl alpha-silyloxyalkyl ketones

被引:29
作者
Figueras, S [1 ]
Martin, R [1 ]
Romea, P [1 ]
Urpi, F [1 ]
Vilarrasa, J [1 ]
机构
[1] UNIV BARCELONA,FAC QUIM,DEPT QUIM ORGAN,E-08028 BARCELONA,CATALONIA,SPAIN
关键词
D O I
10.1016/S0040-4039(97)00108-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldol-like reactions of titanium enolates derived from alpha-OH, alpha-OBn, and alpha-OTBS ketones with a series of aldehydes have been studied. In sharp contrast to the O-benzyl derivatives, the TBS-protected ketones lead to excellent yields and selectivities (syn-syn/anti-syn ratios from 30:1 to > 95:1) even for the lactate-derived substrate (2-tert-butyldimethylsilyloxy-3-pentanone). (C) 1997 Elsevier Science Ltd.
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页码:1637 / 1640
页数:4
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