Organocatalytic Asymmetric Morita–Baylis–Hillman Reaction of Isatins with Vinyl Sulfones

The organocatalytic asymmetric Morita–Baylis–Hillman (MBH) reaction of isatin derivatives with various vinyl sulfones is disclosed. Chiral sulfone-containing 3-hydroxyoxindoles were produced in good to high yields and with good to high ee’s. This report displays an unprecedented example to apply act...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-03, Vol.88 (6), p.3802-3807
Main Authors: He, Hong-Jiao, Wang, Rui-Qi, Wan, Lin-Xi, Zhou, Li-Yan, Li, Hong-Yan, Li, Guo-Bo, Xiao, You-Cai, Chen, Fen-Er
Format: Article
Language:English
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Summary:The organocatalytic asymmetric Morita–Baylis–Hillman (MBH) reaction of isatin derivatives with various vinyl sulfones is disclosed. Chiral sulfone-containing 3-hydroxyoxindoles were produced in good to high yields and with good to high ee’s. This report displays an unprecedented example to apply activated alkenes with sulfone moiety other than carbonyl groups in asymmetric MBH reactions and provides an efficient strategy to incorporate the sulfone functional group for the synthesis of chiral 3-hydroxyoxindoles.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c03073