Highly stereoselective addition of silylphosphines to chiral aldehydes

The reaction between diphenyl(trimethylsilyl)phosphine and chiral aldehydes proceeds with high stereoselectivity to give diastereomerically pure tertiary α-trimethylsiloxyalkylphosphines. The diastereomeric purity of the addition products was 90–100%. The products were purified via the formation of borane–phosphine complexes. The reaction of bis(trimethylsilyl)phenylphosphine with acetonide (R)-glyceraldehyde provides tertiary bis(glyceryl)phosphines.