56377-45-8Relevant articles and documents
Highly enantio- and diastereoselective boron aldol reactions of α-heterosubstituted thioacetates with aldehydes and silyl imines
Gennari, Cesare,Vulpetti, Anna,Pain, Gilles
, p. 5909 - 5924 (2007/10/03)
Boron enolates derived from α-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 α-halothioacetate and bearing menthone-derived chiral ligands react with imines with excellent diastero- and enantiocontrol to give syn α-halo-β-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.