Stereoselective Addition of Grignard Reagents to New P-Chirogenic N-Phosphinoylbenzaldimines: Effect of the Phosphorus Substituents on the Stereoselectivity.

Date publication

juillet 2011

Auteurs

Membres identifiés du Cancéropôle Est :
Dr WAGNER Alain

Tous les auteurs :
Francesco IN, Egloff C, Wagner A, Colobert F

Résumé

Several phosphinoylimines have been synthesized in five steps by starting from the appropriate phosphane oxide and were then treated with methylmagnesium bromide to give both diastereoisomers in high yields and with promising diastereomeric ratios. Then N-[(tert-butyl)(phenyl)phosphinoyl]benzaldimine, which displayed the best results, was subjected to the 1,2-addition of various Grignard reagents to evaluate the best chiral induction due to the stereogenic phosphorus atom. The corresponding adducts were obtained in excellent yields and with moderate to excellent diastereoisomeric ratios.

Référence

. 2011 Jul;20-21:4037-45.