Stereoselective Synthesis of Highly Substituted Cyclohexanes by a Rhodium-Carbene Initiated Domino Sequence

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• 作者：Brendan T. Parr ; Huw M. L. Davies
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：February 20, 2015
• 年：2015
• 卷：17
• 期：4
• 页码：794-797
• 全文大小：328K
• ISSN：1523-7052

文摘

A stereoselective synthesis of cyclohexanes bearing four stereocenters from vinyldiazoacetates and allyl alcohols by a rhodium-carbene initiated domino reaction is described. The reaction cascade features a tandem ylide formation/[2,3]-sigmatropic rearrangement, oxy-Cope rearrangement, and type II carbonyl ene reaction, all of which proceed with a high degree of stereocontrol. The products are routinely isolated with excellent stereocontrol (>97:3 dr, 99% ee).