Asymmetric Intramolecular Aza-Michael Reaction in Desymmetrization Processes. Total Synthesis of Hippodamine and epi-Hippodamine

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• 作者：Marta Guerola ; Mar铆a S谩nchez-Rosell贸 ; Cristina Mulet ; Carlos del Pozo ; Santos Fustero
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：February 20, 2015
• 年：2015
• 卷：17
• 期：4
• 页码：960-963
• 全文大小：337K
• ISSN：1523-7052

文摘

The use of chiral sulfinyl amines both as nucleophilic nitrogen sources and chiral inducers has been described for the first time in a desymmetrization-type process involving an intramolecular aza-Michael reaction. The resulting product was employed as an advanced intermediate in the total synthesis of the natural product hippodamine and epi-hippodamine, taking advantage of the special symmetry of these molecules. In addition, this is the first asymmetric total synthesis of epi-hippodamine.