文献类型：期刊文献

英文题名：Organocatalytic enantioselective β-functionalization of aldehydes by oxidation of enamines and their application in cascade reactions

作者：Zhang, Shi-Lei[1,2];Xie, He-Xin[2];Zhu, Jin[3];Li, Hao[1];Zhang, Xin-Shuai[2];Li, Jian[3];Wang, Wei[1,2,3]

机构：[1]Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China;[2]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA;[3]E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

年份：2011

卷号：2

外文期刊名：NATURE COMMUNICATIONS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000289982600001)】；

基金：Financial support for this work provided by the 'Thousand talent' program of China (W.W.), State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica (W.W.), the China 111 Project (Grant B07023, J.L. and W.W.) and NSF (CHE-0704015, W.W.) is gratefully acknowledged. We are grateful for Professor Patrick Mariano for his editing the manuscript.

语种：英文

摘要：Iminium catalysis, involving the transformation of iminium ions to enamines, has been extensively studied in the context of a number of organic processes. However, the reverse of this process involving conversion of enamines to iminium species has not been realized. Here, we describe a new transformation-'oxidative enamine catalysis'-in which direct oxidation of an enamine occurs to generate an iminium species. We show that the use of o-iodoxybenzoic acid as an oxidant in the presence of a secondary amine catalyst serves as effective system for promoting rapid conversion of enamines to iminium ions. The preparative power of this process has been demonstrated in the context of direct asymmetric beta-functionalization of simple aldehydes. Moreover, a variety of enantioselective cascade transformations, including triple and quadruple cascades, have been developed for the 'one-pot' synthesis of versatile chiral building blocks and structural frameworks starting with simple aldehydes.