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Issue 21, 2015
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Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction

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Abstract

Treatment of diarylphosphinous acid-borane amides possessing chiral amido functionality with an alkali metal solution in liquid ammonia induced a preferential dearomatization of one aryl substituent at phosphorus leading to the formation of non-equimolar amounts of diastereomers. Diastereoselectivity of dearomatization depends strongly on the structure of a chiral auxiliary.

Graphical abstract: Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction

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Publication details

The article was received on 20 Nov 2014, accepted on 15 Dec 2014 and first published on 15 Dec 2014


Article type: Paper
DOI: 10.1039/C4OB02440K
Citation: Org. Biomol. Chem., 2015,13, 6082-6102
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    Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction

    M. Stankevič, Org. Biomol. Chem., 2015, 13, 6082
    DOI: 10.1039/C4OB02440K

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