Generation of chiral boron enolates by rhodium-catalyzed asymmetric 1,4-addition of 9-aryl-9-borabicyclo[3.3.1]nonanes (B-Ar-9BBN) to α,β-unsaturated ketones

被引：44

作者：

Yoshida, K ^{[1
]}

Ogasawara, M ^{[1
]}

Hayashi, T ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 05期

关键词：

D O I：

10.1021/jo020659i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric 1,4-addition of 9-phenyl-9-borabicyclo[3.3.1]nonane (2m) to 2-cyclohexenone (1a) proceeded with high enantioselectivity in toluene at 80 degreesC in the presence of 3 mol % of a rhodium catalyst generated from [Rh(OMe)(cod)](2) and (S)-binap to give a high yield of boron enolate (S)-3am, which is 98% enantiomerically pure. Reaction of the boron enolate 3am with electrophiles, methanol-d, propanal, and allyl bromide, gave the corresponding 2-substituted (3S)-3-phenylcyclohexanones with perfect regio- and diastereoselectivity.

引用

页码：1901 / 1905

页数：5

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