Boron enolates derived from alpha-heterosubstituted thioacetates and bearing menthone-derived chiral ligands react with aldehydes to give anti aldols with excellent diastero- and enantiocontrol. 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. (C) 1997 Elsevier Science Ltd.
Highly enantio- and diastereoselective boron aldol reactions of alpha-heterosubstituted thioacetates with aldehydes and silyl imines / C.M.A. Gennari, A. Vulpetti, G. Pain. - In: TETRAHEDRON. - ISSN 0040-4020. - 53:16(1997), pp. 5909-5924.
Highly enantio- and diastereoselective boron aldol reactions of alpha-heterosubstituted thioacetates with aldehydes and silyl imines
C.M.A. GennariPrimo
;
1997
Abstract
Boron enolates derived from alpha-heterosubstituted thioacetates and bearing menthone-derived chiral ligands react with aldehydes to give anti aldols with excellent diastero- and enantiocontrol. 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. (C) 1997 Elsevier Science Ltd.
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