Influence of an ortho-sulfinyl group on the configurational stability of α-lithiated aryloxiranes: deuteration of tolylsulfinyl styrene oxides |
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| Authors: | Vito Capriati Renzo Luisi Maria Giovanna Tocco José Luis García Ruano Esther Torrente |
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| Institution: | a Dipartimento Farmaco-Chimico, Università di Bari, Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi C.I.N.M.P.I.S, Via Edoardo Orabona 4, I-70125 Bari, Italy
b Departamento de Química Orgánica (C-I), Universidad Autònoma, Cantoblanco, 28049 Madrid, Spain |
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| Abstract: | The influence of the p-tolylsulfinyl group, located at ortho-, meta-, and para-position, on the regio- and stereoselectivity of the deuteration reactions of substituted styrene oxides has been investigated. The sulfinyl group at an ortho-position reduces the configurational stability of α-lithiated styrene oxides, whereas meta- and para-sulfinyl derivatives completely control the regioselectivity only yielding deuterated products at the aromatic ring due to its strong ortho-director effect. |
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| Keywords: | Lithiation Phenyl sulfinyl styrene oxide Configurational stability |
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