Modular Asymmetric Synthesis of Functionalized Azaspirocycles Based on the Sulfoximine Auxiliary

详细信息    查看全文

• 作者：Adeline Adrien ; Hans-Joachim Gais ; Franz Kö ; hler ; Jan Runsink ; Gerhard Raabe
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：May 24, 2007
• 年：2007
• 卷：9
• 期：11
• 页码：2155 - 2158
• 全文大小：97K
• 年卷期：v.9,no.11(May 24, 2007)
• ISSN：1523-7052

文摘

A modular asymmetric synthesis of the functionalized azaspirocycles 6 (m = 2, n = 1), 7 (m = 1, n = 2), 8 (m = n = 2), 12, 20, and 24 fromthe cyclic allylic sulfoximines 1 is described. The synthetic strategy is based on the stereoselective construction of the carbocycle 4 containingthe amino-substituted tertiary C atom from 1 followed by the generation of the azaspirocycle. Three different routes have been followed forthe synthesis of the heterocyclic ring: N,C-dianion cycloalkylation, ring-closing metathesis, and N-acyl iminium ion formation.