The catalytic asymmetric Abramov reaction

Abstract

The first catalytic enantioselective Abramov reaction is described. The process is based on the utilization of a chiral disulfonimide catalyst, which efficiently avoids the difficulties encountered with metal-based catalysts. Several functionalized α-hydroxy phosphonates were synthesized in good yields and with excellent enantiomeric ratios of up to >99:1. The process was shown to be scalable and up to 1 g of starting material could be employed under mild reaction conditions.

Keywords: Abramov reaction; disulfonimides; hydrophosphonylations; organocatalysis; α-hydroxy phosphonates.