Scope and limitations of chiral B-[3,5-bis(trifluoromethyl)phenyl]oxazaborolidine catalyst for use in the Mukaiyama aldol reaction

被引：63

作者：

Ishihara, K

Kondo, S

Yamamoto, H ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, JST, CREST, Nagoya, Aichi 4648603, Japan

[2] Nagoya Univ, ResCWE, Nagoya, Aichi 4648603, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 26期

关键词：

D O I：

10.1021/jo001271v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new chiral oxazaborolidine catalyst was prepared in situ from 3,5-bis(trifluoromethyl)phenylboron dichloride and N-(p-toluenesulfonyl)-(S)-tryptophan. This catalyst is much more active than Corey's original catalyst for the Mukaiyama aldol reaction of aldehydes with silyl enol ethers. The observed syn selectivities and re-face attack of silyl enol ethers on carbonyl carbon of aldehydes imply that the extended-transition state model is applicable.

引用

页码：9125 / 9128

页数：4

共 59 条

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