Tetrahedron Letters p. 9259 - 9262 (1996)
Update date:2022-08-02
Topics:
Paz, Manuel M.
Correa, Juan F.
Cabeza, M. Isabel
Sardina, F. Javier
An efficient (21% overall yield), enantio- and diastereoselective, 11-step synthesis of (1S,2R)-imidazoleglycerol has been developed. The key steps are the stereoselective hydroxylation of an acyloxazolidinone enolate, the alkylation of a thioester with (MOMOCH2)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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