A versatile, enantioselective, stereocontrolled synthesis of (1S,2R)-imidazoleglycerol

An efficient (21% overall yield), enantio- and diastereoseleclive, 11-step synthesis of (1 S ,2 R )-imidazoleglycerol has been developed. The key steps are the stereoselective hydroxylation of an acyloxazolidinone enolate, the alkylation of a thioester with (MOMOCH 2 ) 2 CuLi and the stereodivergent reduction of the resulting ketone. The scope of the reaction of the enolate derived from 10 with heteroatom electrophiles has been studied.