First asymmetric Abramov-type phosphonylation of aldehydes with trialkyl phosphites catalyzed by chiral Lewis bases

Chiral phosphine oxides (Lewis bases) catalyze silicon tetrachloride-mediated, enantioselective phosphonylation of aldehydes with trialkyl phosphites (Abramov-type reaction), which leads to optically active alpha-hydroxyphosphonates with moderate enantioselectivities. (31)P NMR analysis of the phosphonylation of benzaldehyde with triethyl phosphite supports the assumed reaction mechanism. (c) 2008 Elsevier Ltd. All rights reserved.