title: Diastereoselective synthesis of bulky, strongly nucleophilic, and configurationally stable P-stereogenic tricyclic phosphines.
abstract: A very simple, one-step highly diastereoselective synthesis of bulky, configurationally and air-stable P-chiral tricyclic phosphines 3, showing an exceptionally strong nucleophilic character, has been developed. This method involves the reaction of the stable phosphonium sila-ylide 1 with aryl- and alkyl-substituted acetylene derivatives. Starting from commercially available chiral (R,S)-(+)-endo-2-norborneol, the corresponding enantiomerically pure phosphines were obtained with excellent enantioselectivities (ee ≥ 99%) and high chemical yields.
authors.affiliation: Université de Toulouse, UPS, LHFA, 118 route de Narbonne, F-31062 Toulouse, France.
authors.forename: David
authors.initials: D
authors.lastname: Gau
authors.forename: Ricardo
authors.initials: R
authors.lastname: Rodriguez
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Kato
authors.forename: Nathalie
authors.initials: N
authors.lastname: Saffon-Merceron
authors.forename: Antoine
authors.initials: A
authors.lastname: Baceiredo