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Issue 80, 2012
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Identification of a key intermediate in the asymmetric Appel process: one pot stereoselective synthesis of P-stereogenic phosphines and phosphine boranes from racemic phosphine oxides

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Abstract

Sequential treatment of racemic phosphine oxides with oxalyl chloride and chiral non-racemic alcohol generates the same ratios of diastereomeric alkoxyphosphonium salts obtained in the corresponding asymmetric Appel process, strongly implicating the intermediate chlorophosphonium salt in the stereoselecting step. Subsequent reduction allows a novel synthesis of enantioenriched P-stereogenic phosphines–phosphine boranes.

Graphical abstract: Identification of a key intermediate in the asymmetric Appel process: one pot stereoselective synthesis of P-stereogenic phosphines and phosphine boranes from racemic phosphine oxides

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Publication details

The article was received on 08 Jun 2012, accepted on 15 Aug 2012 and first published on 16 Aug 2012


Article type: Communication
DOI: 10.1039/C2CC34136K
Citation: Chem. Commun., 2012,48, 10040-10042
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    Identification of a key intermediate in the asymmetric Appel process: one pot stereoselective synthesis of P-stereogenic phosphines and phosphine boranes from racemic phosphine oxides

    K. V. Rajendran and D. G. Gilheany, Chem. Commun., 2012, 48, 10040
    DOI: 10.1039/C2CC34136K

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