Directed ortho Metalation Reactions of Aryl O-Carbamates; A Regiospecific Synthesis of 2,2-Disubstituted 2H-1-Benzopyrans

Brian A. Chauder; Alexey V. Kalinin; Victor Snieckus

doi:10.1055/s-2001-9747

Synthesis 2001; 2001(1): 0140-0144
DOI: 10.1055/s-2001-9747

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Directed ortho Metalation Reactions of Aryl O-Carbamates; A Regiospecific Synthesis of 2,2-Disubstituted 2H-1-Benzopyrans

Brian A. Chauder^* , Alexey V. Kalinin, Victor Snieckus

^*Queen's University, Kingston, ON, Canada, K7L 3N6; Fax +(613)5 33 28 37; E-mail: snieckus@chem.queensu.ca

Abstract

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A one-pot regiocontrolled synthesis of 2,2-disubstituted 2H-1-benzopyrans 5 from aryl O-carbamates 4 using the directed ortho metalation reaction is described and constitutes an advantageous complement to classical routes for this class of heterocycles.

2H-1-benzopyran - chromene - directed ortho metalation - aryl-O-carbamates - carbamoyl migration

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