Palladium/Brønsted-Acid-Catalyzed Diastereoselective Cyclization with Chiral Sulfinamides as Nucleophiles

This article reports diastereoselective cyclization with chiral sulfinamides as nucleophiles in two reaction pathways: (1) intramolecular allylic substitution and (2) sequential aerobic oxidation with aza-Michael addition. These reactions were enabled by synergistic palladium and Brønsted acid catal...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-09, Vol.86 (17), p.12354-12366
Main Authors: Hung, Chun-Tai, Lu, Chun-Wei, Huang, Shi-Han, Lu, Yin-Feng, Chou, Hsiang-Chi, Tsai, Cheng-Che
Format: Article
Language:English
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Summary:This article reports diastereoselective cyclization with chiral sulfinamides as nucleophiles in two reaction pathways: (1) intramolecular allylic substitution and (2) sequential aerobic oxidation with aza-Michael addition. These reactions were enabled by synergistic palladium and Brønsted acid catalysis and produced chiral isoindolines with good yields of 55–92% and high diastereoselectivities of 10:1 to >20:1 dr.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01301