Boron enolates derived from tert-butyl alpha-halothioacetate and bearing menthone-derived chiral ligands react with imines with excellent diastero- and enantiocontrol to give syn alpha-halo-beta-aminothioesters, which can be converted to the corresponding aziridines by simple ring closure during LAH reduction. A key precursor of antibiotics (+)-thiamphenicol and (-)-florfenicol was synthesized. Copyright (C) 1996 Elsevier Science

Boron aldol reaction of alpha-halosubstituted thioacetates with silyl imines: A highly enantio- and diastereoselective synthesis of aziridines / C.M.A. Gennari, G. Pain. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 37:21(1996), pp. 3747-3750.

Boron aldol reaction of alpha-halosubstituted thioacetates with silyl imines: A highly enantio- and diastereoselective synthesis of aziridines

C.M.A. Gennari
Primo
;
1996

Abstract

Boron enolates derived from tert-butyl alpha-halothioacetate and bearing menthone-derived chiral ligands react with imines with excellent diastero- and enantiocontrol to give syn alpha-halo-beta-aminothioesters, which can be converted to the corresponding aziridines by simple ring closure during LAH reduction. A key precursor of antibiotics (+)-thiamphenicol and (-)-florfenicol was synthesized. Copyright (C) 1996 Elsevier Science
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/177119
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