Carbene-Catalyzed [4+2] Cycloaddition of Cyclobutenones and Isatins for Quick Access to Chiral Chlorine-Containing Spirocyclic δ‑Lactones

Here we report a carbene-catalyzed enantio- and diastereoselective [4+2] cycloaddition reaction of cyclobutenones with isatins for the quick and efficient synthesis of spirocyclic δ-lactones bearing a chiral chlorine. A broad range of substrates with various substitution patterns proceed smoothly in...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-05, Vol.89 (10), p.7286-7294
Main Authors: Liu, Bin, Zhou, Xian, Liu, Qinqin, Yang, Zaihui, Mao, Yuanhu, He, Qing, Zhang, Tianyuan, Kong, Xiangkai, Zhang, Jiquan, Liao, Weike, Tang, Lei
Format: Article
Language:English
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Summary:Here we report a carbene-catalyzed enantio- and diastereoselective [4+2] cycloaddition reaction of cyclobutenones with isatins for the quick and efficient synthesis of spirocyclic δ-lactones bearing a chiral chlorine. A broad range of substrates with various substitution patterns proceed smoothly in this reaction, with the spirooxindole δ-lactone products afforded in generally good to excellent yields and optical purities under mild reaction conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.4c00295