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Indexed by:期刊论文

First Author:Zhu, Guodong

Correspondence Author:Wang, BM (reprint author), Dalian Univ Technol, Sch Pharmaceut Sci & Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China.

Co-author:Wei, Qian,Chen, Hongbo,Zhang, Yanpeng,Shen, Wen,Qu, Jingping,Wang, Baomin

Date of Publication:2017-04-07

Journal:ORGANIC LETTERS

Included Journals:SCIE、PubMed

Volume:19

Issue:7

Page Number:1862-1865

ISSN No.:1523-7060

Abstract:A general and practical organocatalytic asymmetric 1,3-dipolar cycloaddition of 3-amino oxindole-based azomethine ylides and alpha,beta-enones has been developed. This reaction delivered spiro[pyrrolidine-2,3'-oxindole] products in high yields with excellent regio- and enantioselectivities (up to 99% yield, >20:1 rr, 99% ee). In addition, an array of spiro[dihydropyrrole-2,3'-oxindoles] were readily accessed by oxidative dehydrogenation. Notably, the inversion of the diastereoselectivity of the spiro[pyrrolidine-oxindole] product could be easily achieved through a facile oxidation-reduction process.