Synthesis of the first chiral phosphorous chelate aminophosphino-carbene complex and its applications in stereoselective addition reactions

The first phosphorous chelate chiral aminophosphinomethyl carbene complex [cyclic] (OC)4Cr:C(Me)N(Me)CH2CH(Ph)PPh2 5 was synthesized. Its conjugate base represents a new chiral ?-unsubstituted amide enolate equiv. for stereoselective addn. reactions. The structure of the major diastereoisomer of the aldol addn. complex between 5 and p-O2NC6H4CHO, solved by x-ray diffraction, shows that the (S)-enantiomer of the conjugated base of 5 reacts preferentially with the re face of the carbonyl function