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

Gilheany, Declan G.Declan G.GilheanyRajendran, Kamalraj V.Kamalraj V.Rajendran2013-11-152013-11-15Royal Soci2012-08Chemical Communicationshttp://hdl.handle.net/10197/4930Sequential 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.endynamic resoln. of phosphine oxides by one-pot Appel chlorination-alkoxylation with chiral alcs.prepn. of chiral phosphines and phosphine-boranes by redn.ChiralIdentification of a key intermediate in the asymmetric Appel process: one pot stereoselective synthesis of P-stereogenic phosphines and phosphine boranes from racemic phosphine oxidesJournal Article4880100401004210.1039/c2cc34136k2013-10-10https://creativecommons.org/licenses/by-nc-nd/3.0/ie/