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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Title: 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
Authors: Gilheany, Declan G.
Rajendran, Kamalraj V.
Permanent link: http://hdl.handle.net/10197/4930
Date: Aug-2012
Abstract: Sequential treatment of racemic phosphine oxides with oxalylchloride and chiral non-racemic alcohol generates the sameratios of diastereomeric alkoxyphosphonium salts obtained inthe corresponding asymmetric Appel process, strongly implicatingthe intermediate chlorophosphonium salt in the stereoselectingstep. Subsequent reduction allows a novel synthesis of enantioenriched P-stereogenic phosphines-phosphine boranes.
Funding Details: Science Foundation Ireland
Other funder
Type of material: Journal Article
Publisher: Royal Society of Chemistry
Copyright (published version): Royal Society of Chemistry 2012
Keywords: dynamic resoln. of phosphine oxides by one-pot Appel chlorination-alkoxylation with chiral alcs.prepn. of chiral phosphines and phosphine-boranes by redn.Chiral
DOI: 10.1039/c2cc34136k
Language: en
Status of Item: Peer reviewed
Appears in Collections:Chemistry Research Collection

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