Chiral N-Heterocyclic Carbene-Catalyzed Asymmetric Michael-Intramolecular Aldol-Lactonization Cascade for Enantioselective Construction of [beta]-Propiolactone-Fused Spiro[cyclopentane-oxindoles]

A cascade asymmetric Michael-intramolecular aldol-lactonization of enals with oxindolyl [beta],[gamma]-unsaturated [alpha]-keto esters was developed. An optically pure aminoindanol-derived triazolium-based N-heterocyclic carbene was used as the catalyst. The corresponding desired [beta]-propiolacton...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-05, Vol.359 (9), p.1541
Main Authors: Zhang, Jun-Qi, Li, Nai-Kai, Yin, Shao-Jie, Sun, Bing-Bing, Fan, Wei-Tai, Wang, Xing-Wang
Format: Article
Language:English
Subjects:
Aldehydes
Asymmetry
Catalysts
Esters
Online Access:Get full text
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Summary:A cascade asymmetric Michael-intramolecular aldol-lactonization of enals with oxindolyl [beta],[gamma]-unsaturated [alpha]-keto esters was developed. An optically pure aminoindanol-derived triazolium-based N-heterocyclic carbene was used as the catalyst. The corresponding desired [beta]-propiolactone-fused spiro[cyclopentane-oxindoles] were obtained in moderate yields with excellent diastereoselectivities and enantioselectivities. Notably, the obtained enantio-enriched highly functionalized complex molecules contain four contiguous stereocenters, including a spiro all-carbon center and a quaternary carbon center.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201601259