Enantioselective synthesis of β-amino alcohols and α-amino acids via a copper catalyzed addition of diorganozinc reagents to N-phosphinoylimines

JN Desrosiers, A Côté, AB Charette

Index: Desrosiers, Jean-Nicolas; Cote, Alexandre; Charette, Andre B. Tetrahedron, 2005 , vol. 61, # 26 p. 6186 - 6192

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Citation Number: 51

Abstract

Enantioenriched β-amino alcohols were prepared via an asymmetric addition of diethylzinc, catalyzed by the BozPHOS· Cu (I) complex, on in situ formed N-phosphinoylimines. The nature of the hydroxyl protecting groups was found to affect the enantioselectivities. Subsequent deprotection and oxidation of N-phosphinoyl β-amino alcohols afforded optically active α-amino acids (97% ee).