Asymmetric Organocatalytic Allylic Substitution of Morita鈥揃aylis鈥揌illman Carbonates with Allylamines for the Synthesis of 2,5-Dihydropyrroles

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• 作者：Wangsheng Sun ; Xiaozhou Ma ; Liang Hong ; Rui Wang
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：October 7, 2011
• 年：2011
• 卷：76
• 期：19
• 页码：7826-7833
• 全文大小：895K
• 年卷期：v.76,no.19(October 7, 2011)
• ISSN：1520-6904

文摘

The asymmetric allylic substitution reaction of MBH carbonates with allylamines has been developed, which affords N-allyl-尾-amino-伪-methylene esters in high yields and enantioselectivities. After a subsequent ring-closure metathesis of the products, a series of optically active 2,5-dihydropyrroles could be obtained smoothly in high yields without any loss of enantioselectivity. Finally, a tentative mechanism for rationalization of the reaction has been proposed.