Diastereoselective synthesis of bulky, strongly nucleophilic, and configurationally stable P-stereogenic tricyclic phosphines.
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.
Gau
David
D
Université de Toulouse, UPS, LHFA, 118 route de Narbonne, F-31062 Toulouse, France.
Rodriguez
Ricardo
R
Kato
Tsuyoshi
T
Saffon-Merceron
Nathalie
N
Baceiredo
Antoine
A