Organocatalytic Enantioselective Formal [4 + 2] Cycloaddition of Enones with Cyclic N-Sulfonylimines and Methylene Chromene for Chiral Spirocyclic Compounds

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• 作者：Jie Fei ; Qingqing Qian ; Xiaohua Sun ; Xiaodong Gu ; Chuncheng Zou ; Jinxing Ye
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：17
• 期：21
• 页码：5296-5299
• 全文大小：370K
• ISSN：1523-7052

文摘

A highly enantioselective synthesis of spirocycles and bridged rings has been developed through a formal [4 + 2] cycloaddition reaction between enones and N-sulfonylimines. The unprecedented strategy has been realized utilizing N-sulfonylimine as a novel dienophile through enamine鈥搃minium tautomerism of N-sulfonylimine. In addition, a 纬,蔚-regioselective cycloaddition reaction proceeded by employing methylene chromene species as dienophiles.