Efficient asymmetric synthesis of trifluoromethylated β-aminophosphonates and their incorporation into dipeptides

摘要

Addition of anions derived from dialkyl methylphosphonates to (Ss)-N-tert-butanesulflnyl (3,3,3)-trifluoroacetaldimine afforded (Ss,R) addition adducts in moderate to good yield (53-75%) with excellent diastereoselectivity (94-95% de). After selective removal of the A'-sulfinyl group, dipeptides containing enantio-merically pure diethyl 2-amino-3,3,3-trifluoropropylphosphonate were synthesized to investigate the influence of the trifluoromethyl substituent on TV-terminal coupling.