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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 184, 2009 - Issue 5: Honoring the 70th Birthday of Marian Mikolajczyk, Part 2
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Original Articles

Stereoselective Chemo-Enzymatic Approaches to the Synthesis of C2 1,3-Dithiane-1,3-dioxide

N. Gaggero Istituto di Chimica Organica “A. Marchesini”, Milano, Italy
,
S. Colonna Istituto di Chimica Organica “A. Marchesini”, Milano, Italy
,
D. Albanese Dipartimento di Chimica Organica e Industriale, Milano, Italy
,
G. Ottolina Istituto di Chimica del Riconoscimento Molecolare–CNR, Milano, Italy
&
F. Del Monte Istituto di Chimica Organica “A. Marchesini”, Milano, Italy
Pages 1332-1339 | Received 31 Jan 2008, Accepted 14 Feb 2008, Published online: 28 Apr 2009
 
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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-dioxide is described. The target molecule is obtained with enantiomeric excesses up to 90%.

Dedicated to Professor Marian Mikołajczyk, CBMiM PAN in Łódź, Poland, on the occasion of his 70th birthday.

Notes

a Determined by 1H NMR spectroscopy.

b Determined by HPLC.

c Pig liver esterase.

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