Stereoselective Chemo-Enzymatic Approaches to the Synthesis of C 2 1, 3-Dithiane-1, 3-dioxide

…, D Albanese, G Ottolina, F Del Monte

Index: Gaggero; Colonna; Albanese; Ottolina; Del Monte Phosphorus, Sulfur and Silicon and the Related Elements, 2009 , vol. 184, # 5 p. 1332 - 1339

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Abstract

Two enzyme-mediated methods are presented for the preparation of enantiomerically enriched C 2 1, 3-dithiane-1, 3-dioxide. The first takes advantage of a trans stereoselective oxidation by NaIO 4 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- ...