Catalyst-Controlled Divergent Reactions of 2,3-Disubstituted Indoles with Propargylic Alcohols: Synthesis of 3-Benzo[]azepines and Axially Chiral Tetrasubstituted Allenes.

Org Lett

Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, Southern University of Science and Technology (SUSTech), Shenzhen, Guangdong 518055, China.

Published: September 2022

Catalyst-controlled divergent reactions of 2,3-disubstituted indoles with propargylic alcohols were developed for the first time. In the presence of TsOH or B(CF) as catalyst, 2,3-disubstituted indoles reacted smoothly with 3-alkynyl-3-hydroxyisoindolinones to afford 3-benzo[]azepines by selective C2(sp)-C3(sp) ring expansion of indoles. In contrast, decreasing the catalyst strength (e.g., with chiral phosphoric acid) interrupted the cascade reactions, affording axially chiral tetrasubstituted allenes bearing an adjacent chiral quaternary carbon stereocenter. Control experiments provided insights into the reaction mechanism.

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http://dx.doi.org/10.1021/acs.orglett.2c02642DOI Listing

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