Organic Chemistry Portal

Abstracts

Search:

Catalytic Enantioselective Allylboration and Related Reactions of Isatins Promoted by Chiral BINOLs: Scope and Mechanistic Studies

Julien Braire, Aurélie Macé, Rania Zaier, Marie Cordier, Joëlle Vidal*, Claudia Lalli*, Arnaud Martel* and François Carreaux*

*Univ Rennes, F-35000 Rennes; Université du Maine, 72085 Cedex Le Mans, France, Email: joelle.vidaluniv-rennes1.fr, claudia.lalliuniv-rennes1.fr, arnaud.marteluniv-lemans.fr, francois.carreauxuniv-rennes1.fr

J. Braire, A. Macé, R. Zaier, M. Cordier, J. Vidal, C. Lalli, A. Martel, F. Carreaux, J. Org. Chem., 2023, 88, 1457-1468.

DOI: 10.1021/acs.joc.2c02476


see article for more reactions

Abstract

Chiral BINOL derivatives catalyze an enantioselective allylboration of isatins with 2-allyl-1,3,2-dioxaborolane to provide enantioenriched N-unprotected 3-allyl-3-hydroxy-2-oxindoles. This catalytic process is also effective for asymmetric crotylboration reactions, as well as for the enantioselective synthesis of homopropargylic alcohols.

see article for more examples


proposed mechanisms



Key Words

isatins, 2-oxindoles, organocatalysis


ID: J42-Y2023