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Asymmetric [3+2] Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and alpha,beta-Enones with Divergent Diastereocontrol on the Spiro[pyrrolidine-oxindoles]

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Indexed by:期刊论文

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.

Pre One:Assembly of Indolenines, 3-Amino Oxindoles, and Aldehydes into Indolenine-Substituted Spiro[pyrrolidin-2,3 '-oxindoles] via 1,3-Dipolar Cycloaddition with Divergent Diastereoselectivities

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