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Synthesis (Stuttg). 2015 Jun;47(12):1709-1715.

Iron-Catalyzed Diastereoselective Intramolecular Olefin Aminobromination with Bromide Ion.

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1
Department of Chemistry, Georgia State University, 100 Piedmont Avenue SE, Atlanta, GA 30303, USA.

Abstract

A new iron-catalyzed diastereoselective aminobromination method is reported for both internal and terminal olefins (yield up to 90% and dr up to >20:1). In this transformation, a functionalized hydroxylamine and bromide ion were used as the nitrogen and bromine source, respectively. This method is compatible with a broad range of olefins and provides a convenient approach to synthetically valuable vicinal bromo primary amines. Our studies suggest that both the diastereoselectivity and enantioselectivity for the olefin aminobromination can be controlled by iron catalysts.

KEYWORDS:

alkenes; bromine; diastereoselectivity; iron; nitrogen

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