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Synthesis 2015; 47(12): 1709-1715
DOI: 10.1055/s-0034-1378719
DOI: 10.1055/s-0034-1378719
paper
Iron-Catalyzed Diastereoselective Intramolecular Olefin Aminobromination with Bromide Ion
Further Information
Publication History
Received: 06 April 2015
Accepted after revision: 12 May 2015
Publication Date:
27 May 2015 (online)
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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378719.
- Supporting Information
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References
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For selected reports on catalytic asymmetric olefin aminobromination via an electrophilic bromonium ion, see:
For a reference of asymmetric aminobromination of terminal olefins with bromine radical donors, see:
For iron-catalyzed stereoselective olefin aminohydroxylation and aminofluorination that proceed through an iron-nitrenoid intermediate, see:
For the iron-catalyzed asymmetric aminochlorination method for internal olefins, see:
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