Two enzyme-mediated methods are presented for the preparation of enantiomerically enriched C2 1,3-dithiane-1,3-dioxide. The first takes advantage of a trans stereoselective oxidation by NaIO4 of enantiomerically pure (R) 1,3-dithiane-1-oxide obtained by cyclohexanone monooxygenase. In the second method, a kinetic resolution consisting of a domino hydrolysis-decarboxylation process of (±) 2-carbethoxy-1,3-dithiane- trans-1,3-dioxide is described. The target molecule is obtained with enantiomeric excesses up to 90%.
Stereoselective chemo-enzymatic approaches to the synthesis of C2 1,3-dithiane-1,3-dioxide / N. Gaggero, S. Colonna, D. Albanese, G. Ottolina, F. Del Monte. - In: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS. - ISSN 1042-6507. - 184:5(2009), pp. 1332-1339.
Stereoselective chemo-enzymatic approaches to the synthesis of C2 1,3-dithiane-1,3-dioxide
N. GaggeroPrimo
;S. ColonnaSecondo
;D. Albanese;F. Del MonteUltimo
2009
Abstract
Two enzyme-mediated methods are presented for the preparation of enantiomerically enriched C2 1,3-dithiane-1,3-dioxide. The first takes advantage of a trans stereoselective oxidation by NaIO4 of enantiomerically pure (R) 1,3-dithiane-1-oxide obtained by cyclohexanone monooxygenase. In the second method, a kinetic resolution consisting of a domino hydrolysis-decarboxylation process of (±) 2-carbethoxy-1,3-dithiane- trans-1,3-dioxide is described. The target molecule is obtained with enantiomeric excesses up to 90%.
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