Synthesis of chiral ortho-thio-substituted phenyl phosphonodiamidates via a P-S to P-C rearrangement |
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Authors: | Christelle Mauger |
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Affiliation: | Laboratoire de Chimie Moléculaire et Thio-organique (UMR CNRS 6507), Université de Caen--ENSICAEN, 6 Boulevard Maréchal Juin, 14000 Caen, France |
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Abstract: | The ortho-lithiation of a phenyl phosphorodiamidothioate derived from an enantiopure C2-symmetric diamine is studied. It is shown that the migration of the diaminophosphoryl group from sulfur to carbon, leading to an ortho-sulfanylated phenyl phosphonodiamidate, only occurs in the presence of an alkylating agent or a Lewis acid as BF3·Et2O. The influence of the chiral diaminophosphoryl group on the stereoselectivity of the oxidation of the ortho-sulfanyl or alkylsulfanyl group is also examined. |
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Keywords: | ortho-Lithiation [1,3]-Sigmatropy Phosphorodiamidothioate Phosphonodiamidate Thiol Sulfoxide |
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