Diastereo- and Enantioselective [3 + 2] Cycloaddition Reaction of Morita–Baylis–Hillman Carbonates of Isatins with N-Phenylmaleimide Catalyzed by Me-DuPhos

A Me-DuPhos-catalyzed efficient asymmetric [3 + 2] cycloaddition reaction between Morita–Baylis–Hillman carbonates of isatins and N-phenylmaleimide has been developed. This reaction constructs three chiral centers in one step to afford spirocyclopentaneoxindoles in good yields (up to 84%) with excel...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-04, Vol.77 (8), p.4143-4147
Main Authors: Wang, Yan, Liu, Li, Zhang, Tao, Zhong, Neng-Jun, Wang, Dong, Chen, Yong-Jun
Format: Article
Language:English
Subjects:
Carbonates - chemistry
Catalysis
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Isatin - chemical synthesis
Isatin - chemistry
Maleimides - chemical synthesis
Maleimides - chemistry
Molecular Structure
Organic chemistry
Phosphines - chemistry
Preparations and properties
Stereoisomerism
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Summary:A Me-DuPhos-catalyzed efficient asymmetric [3 + 2] cycloaddition reaction between Morita–Baylis–Hillman carbonates of isatins and N-phenylmaleimide has been developed. This reaction constructs three chiral centers in one step to afford spirocyclopentaneoxindoles in good yields (up to 84%) with excellent diastereo- and enantioselectivies (up to 99% ee).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo3002535