Catalytic asymmetric reactions for organic synthesis: The combined C-H activation/siloxy-cope rearrangement

被引：27

作者：

Davies, HML ^{[1
]}

Beckwith, REJ ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 26期

关键词：

D O I：

10.1021/jo048429m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrakis(N-[4-dodecylbenzenesulfonyl]-(L)-prolinate) dirhodium [Rh-2(S-DOSP)(4)]-catalyzed decomposition of vinyldiazoacetates in the presence of allyl silyl ethers results in the formation of the direct C-H insertion product and the product derived from a combined C-H activation/siloxy-Cope rearrangement. Both products are formed with very high diastereoselectivity (>94% de) and high enantioselectvity (78-93% ee). Under thermal or microwave conditions, the direct C-H insertion product undergoes a siloxy-Cope rearrangement in a stereoselective manner.

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页码：9241 / 9247

页数：7

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