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Effective and Highly Stereoselective Coupling with Vinyldiazomethanes To Form Symmetrical Trienes

鄢明Michael P. Doyle* and Ming Yan

J. Org. Chem. 2002, 67, 602-604,-0001,():

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摘要/描述

Diazo coupling reactions are capable of forming E,E,E-trienes from cinnamaldehydes in good yield. An efficient methodology is reported for the production of styryldiazomethanes that are subsequently used with catalysis for coupling and for cyclopropanation. A vast difference in product selectivity is seen with styryldiazomethane generated from the corresponding hydrazone via manganese dioxide oxidation and that formed in situ by treatment of the tosylhydrazone sodium salt of cinnamaldehyde with transition metal catalysts. This observation impacts understanding of the reaction mechanism for diazo decomposition.

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版权说明:以下全部内容由鄢明上传于   2009年04月20日 10时49分16秒,版权归本人所有。

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