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

Authors :
Chun-Tai Hung
Chun-Wei Lu
Cheng-Che Tsai
Shi-Han Huang
Yin-Feng Lu
Hsiang-Chi Chou
Source :
The Journal of Organic Chemistry. 86:12354-12366
Publication Year :
2021
Publisher :
American Chemical Society (ACS), 2021.

Abstract

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 Bronsted acid catalysis and produced chiral isoindolines with good yields of 55-92% and high diastereoselectivities of 10:1 to >20:1 dr.

Details

ISSN :
15206904 and 00223263
Volume :
86
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....22ee8eea9515101ec86989f17d741a69