Synthesis of enantioenriched 4-thiazolidinone (-)-LY213829 by chemoselective benzylamide cleavage in the presence of a C-S bond

Article abstract of DOI:10.1016/0957-4166(96)00321-7

(R)-2-Methylbenzylamine has been used to covalently 'resolve' thiol acid 7 and assemble 4-thiazolidinone 8a in one step. Selective deprotection of the 2-methylbenzylamide using lithium in ammonia/THF has been achieved in the presence of a readily hydrogen