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Direct Organocatalytic and Highly Enantio- and Diastereoselective Mannich Reactions of α-Substituted α-Cyanoacetates

Authors

  • Thomas B. Poulsen,

    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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  • Carlos Alemparte 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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  • Steen Saaby 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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  • Marco Bella 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. We are grateful to Dr. Jacob Overgaard for X-ray crystallographic analysis.

Abstract

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Metal-free catalysis: Highly functionalized molecules with two contiguous stereocenters are easily accessed in high yield with high enantio- and diastereoselectivity by using a commercially available organocatalyst ((DHQD)2PYR, see scheme). The easily removed Boc protecting group in the product is an added value to this method as an important tool in asymmetric synthesis.

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