The first asymmetric synthesis of alpha-sulfanylphosphonates |
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| Authors: | Marchand P Gulea M Masson S Saquet M Collignon N |
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| Institution: | Laboratoire de Chimie Moléculaire et Thio-organique, UMR 6507-ISMRA-Université de Caen, 6 Bd du Maréchal Juin 14050 Caen Cedex, France. |
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| Abstract: | reaction: see text] Diastereoselectivity of up to 88% was achieved for the synthesis of an alpha-mercapto gamma-unsaturated phosphonate using the readily available chiral dimenthylphosphonyl ester group and a carbanionic 2,3]-sigmatropic rearrangement. Absolute configuration of the newly formed chiral center of this nonracemic thiol was determined, and the corresponding phosphono thiolane and thiolane S-oxide were also stereoselectively prepared. |
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