DOUBLE STEREODIFFERENTIATION IN THE LEWIS-ACID PROMOTED CROTYLATION OF (S)-2-ALKOXYPROPANAL WITH CHIRAL BETA-ALKYL (E)-CROTYLSILANES

被引：21

作者：

JAIN, NF ^{[1
]}

CIRILLO, PF ^{[1
]}

PELLETIER, R ^{[1
]}

PANEK, JS ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 48期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(95)01895-O

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sense and level of 1,2-asymmetric induction have been evaluated in the Lewis acid promoted addition of (E)-crotylsilanes (S)-1 and (R)-2 to (S)-2-alkoxypropanal 3 and 7. These aldehydes are substituted at the alpha-position with benzyloxy (OBn) to reinforce chelation and tert-butyldiphenylsilyloxy (TBDPSO) groups to prevent chelation with bidentate Lewis acids. The nature of the Lewis acid and the chirality of the silane reagent were found to play a pivotal role in the direction and levels of carbonyl diastereoface selectivity.

引用

页码：8727 / 8730

页数：4

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