Asymmetric [3+2] cycloaddition of 3-amino oxindole-based azomethine ylides with alpha,beta-ynones: a straightforward approach to spirooxindoles incorporating 2,5-dihydropyrroles and pyrroles
Release Time:2019-03-12 Hits:
Indexed by: Journal Papers
Date of Publication: 2017-04-30
Journal: CHEMICAL COMMUNICATIONS
Included Journals: PubMed、SCIE
Volume: 53
Issue: 34
Page Number: 4714-4717
ISSN: 1359-7345
Abstract: An organocatalytic asymmetric [3+2] cycloaddition of 3-amino oxindole-based azomethine ylides and alpha,beta-ynones has been developed. This reaction afforded spiro[dihydropyrrole-2,3'-oxindole] products in high chemical yields with excellent stereoselectivities (up to 99% yields, 420 : 1 dr and > 99% ee). Notably, a series of important spiro[pyrrole-oxindole] derivatives were readily obtained via oxidation of the cycloadducts, thus extending the diversity of the products.