ChemInform Abstract: Stereochemistry in Asymmetric Alkylation of Aldimine via Chiral Bis(oxazolyl)phenylplatinum Complexes.

Abstract

Chiral (S,S)-(Phebox)PtCl complex 2 [Phebox = bis(oxazolyl)phenyl] and its cationic complexes (Phebox)Pt(OTf) (3) and [(Phebox)Pt(H2O)](BF4) (4) were synthesized by the transmetalation reaction of (Phebox)SnMe3 (1) with K[PtCl3(C2H4)](H2O) 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 = BF4), which were subjected to alkylation with organolithium reagents resulting in 82% ee of the product amine (S)-10b.