The reaction of an enantiomerically pure sulfinimine of trifluoropyruvate with several metal enolates is described. The use of TiCl(O-iPr)3/LDA produced the corresponding sulfinamides with high stereocontrol. The latter could be smoothly transformed into each enantiomer of a-trifluoromethyl aspartic acid with high ee, which has been previously synthesized only in racemic form.
Stereoselective synthesis of (R)- and (S)-alfa-trifluoromethyl aspartic acid via titanium enolate addition to a sulfinimine of trifluoropyruvate
CRUCIANELLI, MARCELLO;DE ANGELIS, Francesco;
2004-01-01
Abstract
The reaction of an enantiomerically pure sulfinimine of trifluoropyruvate with several metal enolates is described. The use of TiCl(O-iPr)3/LDA produced the corresponding sulfinamides with high stereocontrol. The latter could be smoothly transformed into each enantiomer of a-trifluoromethyl aspartic acid with high ee, which has been previously synthesized only in racemic form.File in questo prodotto:
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