Phosphorous Containing Proline Derivatives for Asymmetric Organocatalysis

Mastay, Andrew, and David Bartley

Proline and proline derivatives are widely used reagents for organocatalysis of asymmetric aldol, Diels-Alder, Mannich, and Michael reactions. Replacing the carboxylic acid of proline with a phosphonic or phosphinic acid functional group allows for the introduction of additional steric hindrance to the acid side chain of the catalyst while maintaining the acid-base catalytic properties of proline. Work toward the synthesis of phosphorus containing proline derivatives will be presented.