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Enantioselective Organocatalyzed α Sulfenylation of Aldehydes

Authors

  • Mauro Marigo,

    1. The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8919-6199
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  • Tobias C. Wabnitz Dr.,

    1. The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8919-6199
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  • Doris Fielenbach Dr.,

    1. The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8919-6199
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  • Karl Anker Jørgensen Prof. Dr.

    1. The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8919-6199
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  • This work was made possible by a grant from The Danish National Research Foundation. M.M. and T.C.W. thank the EU (HMPT-CT-2001-00317) for financial support.

Abstract

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The facile elaboration of optically active α-sulfanyl-substituted aldehydes makes their direct preparation from unmodified aldehydes and 1-benzylsulfanyl-1,2,4-triazole particularly valuable. The substituted aldehydes are formed with excellent enantioselectivities in the presence of sterically demanding chiral pyrrolidine derivatives as organocatalysts (see scheme). R, R′=H, alkyl, allyl, benzyl, Ph.

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