Asymmetric [3+2] Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and alpha,beta-Enones with Divergent Diastereocontrol on the Spiro[pyrrolidine-oxindoles]
Release Time:2019-03-12 Hits:
Indexed by: Journal Article
Date of Publication: 2017-04-07
Journal: ORGANIC LETTERS
Included Journals: PubMed、SCIE
Volume: 19
Issue: 7
Page Number: 1862-1865
ISSN: 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.
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