Asymmetric induction in the addition of enantiomerically pure H-phosphinate to chiral aldimines: diastereoselective generation of α-amino phosphinates with P,C-stereogenic centers

α-Amino phosphinates with P,C-stereogenic centers were prepared from a P-retained addition of (RP)-(−)-menthyl H-phenylphosphinate to (R)-aldimines with up to 86:14 dr under catalyst and solvent free condition at ambient temperature; the single (SP,Sα-C)-stereoisomers were isolated in moderate yields. Chirality on the nitrogen of chiral aldimine was proposed to control the stereoselectivity, and the (−)-menthoxyl showed mismatched asymmetric induction with (S)-aldimines.

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