Chiral diphenylthiophosphoramides: a new class of chiral ligands for the silver(I)-promoted enantioselective allylation of aldehydes

Chiral C-2-symmetric diphenylthiophosphoramides 1 and 2 were prepared in hi gh yields from the reaction of diphenylthiophosphinic chloride with (1R,2R) -(-)-1,2-diaminocyclohexane and (1R,2R)-(+)- 1,2-diphenylethylenediamine, r espectively. Another novel chiral ligand 4 was prepared from reaction of di phenylthiophosphinic chloride with (R)-(+)-1,1'-binaphthyl-2,2'-diamine usi ng butyllithium as a base. They were used as catalytic chiral ligands in th e silver(I)-promoted enantioselective allylation reaction of aldehydes with allyltributyltin. (C) 2000 Elsevier Science Ltd. All rights reserved.