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

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
37
Issue
51
Identifiers
DOI: 10.1016/s0040-4039(96)02138-7

Abstract

Abstract 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) 2CuLi 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.

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