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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

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Indexed by:Journal Papers

Date of Publication:2017-04-30

Journal:CHEMICAL COMMUNICATIONS

Included Journals:SCIE、PubMed

Volume:53

Issue:34

Page Number:4714-4717

ISSN No.: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.

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