Catalytic asymmetric allylic C-H activation as a surrogate of the asymmetric Claisen rearrangement

被引：55

作者：

Davies, HML ^{[1
]}

Ren, PD ^{[1
]}

Jin, QH ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 22期

关键词：

D O I：

10.1021/ol0167255

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Tetrakis[N-[(4-dodecylphenyl)sulfonyl]-(S)-prolinato]-dirhodium [Rh-2(S-DOSP)(4)] catalyzed decomposition of methyl aryldiazoacetates in the presence of alkenes results in allylic C-H activation by means of a rhodium-carbene induced C-H insertion. The resulting gamma,delta -unsaturated esters are equivalent to products that would be traditionally obtained from an asymmetric Claisen rearrangement. Highly regio- and enantioselective C-H insertions can be achieved, and in certain cases, good diastereocontrol is also possible.

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页码：3587 / 3590

页数：4

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