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Synfacts 2008(2): 0202-0202  
DOI: 10.1055/s-2007-992436
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

A New Organocatalyst for the Strecker Reaction

Contributor(s): Benjamin List, Kristina Zumbansen
M. Negru, D. Schollmeyer, H. Kunz*
Universität Mainz, Germany
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

A new organocatalyst has been developed which contains a glycosyl amine and a planar-chiral [2.2]paracyclophane but no hydrogen-bond-donor or Brønsted acidic functionalities. The catalyst was used in an enantioselective Strecker reaction where HCN was generated in situ from Me3SiCN and methanol. Imines derived from aliphatic aldehydes afford products in good yields with high enantioselectivities. The reaction with aromatic aldimines, on the contrary to other reported enantioselectively catalyzed Strecker reactions, gave slightly lower enantioselectivity.