Looking for an appropriated synthetic method for the pharmacologically relevant 1,2-selenoamines1 in optically pure form, we have studied the reactions of N-sulfinylimines with alfa-selenyl carbanions, bearing a remote sulfinyl group as chiral auxiliary. Starting from reagents of identical configuration at sulfur, reactions are completely stereoselective in most of the cases. Resulting compounds were transformed into the desired enantiomerically pure 1,2-selenoamines by C-desulfinylation with t-BuLi and N-desulfinylation with TFA.
Ortho-Sulfinylbenzyl Selenylcarbanions as Nucleophiles. Synthesis of Enantiomerically Pure 1,2-Disubstituted 2-Selenoamines / Alessandro Degl’innocenti; Antonella Capperucci; Lucrezia Frateschi; Jose Luis García Ruano; Ana Maria Martín Castro; Ester Torrente. - STAMPA. - P53:(2010), pp. 189-189. (Intervento presentato al convegno 9th International Symposium on Carbanion Chemistry, ISCC-9 tenutosi a Firenze (Italy) nel July 20-24 2010).
Ortho-Sulfinylbenzyl Selenylcarbanions as Nucleophiles. Synthesis of Enantiomerically Pure 1,2-Disubstituted 2-Selenoamines
CAPPERUCCI, ANTONELLA;
2010
Abstract
Looking for an appropriated synthetic method for the pharmacologically relevant 1,2-selenoamines1 in optically pure form, we have studied the reactions of N-sulfinylimines with alfa-selenyl carbanions, bearing a remote sulfinyl group as chiral auxiliary. Starting from reagents of identical configuration at sulfur, reactions are completely stereoselective in most of the cases. Resulting compounds were transformed into the desired enantiomerically pure 1,2-selenoamines by C-desulfinylation with t-BuLi and N-desulfinylation with TFA.
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