Stereochemistry in Asymmetric Alkylation of Aldimine via Chiral Bis(oxazolyl)phenylplatinum Complexes

Chiral ( S, S )-(Phebox)PtCl complex 2 [Phebox = bis(oxazolyl)phenyl] and its cationic complexes (Phebox)Pt(OTf) ( 3 ) and [(Phebox)Pt(H 2 O)](BF 4 ) ( 4 ) were synthesized by the transmetalation reaction of (Phebox)SnMe 3 ( 1 ) with K[PtCl 3 (C 2 H 4 )](H 2 O) and subsequent treatment with silver salts. Both cationic complexes 3 and 4 readily reacted with N -phenylbenzaldimine ( 7 ) to afford the corresponding chiral aldimine complexes [(Phebox)Pt(aldimine)](X) ( 8, X = OTf; 9, X = BF 4 ), which were subjected to alkylation with organolithium reagents resulting in 82% ee of the product amine ( S )- 10b .