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Iron-Catalyzed Diastereoselective Intramolecular Olefin Aminobromination with Bromide Ion.

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.

SUBMITTER: Tian JS

PROVIDER: S-EPMC4720155 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Iron-Catalyzed Diastereoselective Intramolecular Olefin Aminobromination with Bromide Ion.

Tian Jun-Shan JS Zhu Cheng-Liang CL Chen Yun-Rong YR Xu Hao H

Synthesis 20150601 12

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 enantiosel ...[more]

PMID: 26806984

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