Tandem Asymmetric Cyclopropanation/Cope Rearrangement. A Highly Diastereoselective and Enantioselective Method for the Construction of 1,4-Cycloheptadienes

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• 作者：Huw M. L. Davies ; Douglas G. Stafford ; Brian D. Doan ; and Jeffrey H. Houser
• 刊名：Journal of the American Chemical Society
• 出版年：1998
• 出版时间：April 15, 1998
• 年：1998
• 卷：120
• 期：14
• 页码：3326 - 3331
• 全文大小：258K
• 年卷期：v.120,no.14(April 15, 1998)
• ISSN：1520-5126

文摘

Decomposition of vinyldiazoacetates by rhodium(II)(N-dodecylbenzenesulfonyl)prolinate(Rh₂(S-DOSP)₄, 1) in the presence of dienes results in adirect and highly enantioselective method for theformationof cis-divinylcyclopropanes. Combination of thisprocess with a subsequent Cope rearrangement results in ahighly enantioselective synthesis of a variety of cycloheptadienescontaining multiple stereogenic centers.