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.
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页码：9125 / 9128
页数：4
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