A New Trimeric Cinchona Alkaloid as a Chiral Phase-Transfer Catalyst for the Synthesis of Asymmetric α-Amino Acids

Ayyanar Siva; Eagambaram Murugan

doi:10.1055/s-2005-872170

PAPER

A New Trimeric Cinchona Alkaloid as a Chiral Phase-Transfer Catalyst for the Synthesis of Asymmetric α-Amino Acids

Ayyanar Siva*^a, Eagambaram Murugan^b
^a Department of Chemistry, Gandhigram Rural Institute-Deemed University, Gandhigram 624 302, TN, India
^b Department of Physical Chemistry, University of Madras, Guindy Campus, Chennai 600 025, TN, India
Fax: +91(451)2453071; e-Mail: ptcsiva@yahoo.co.in;

Abstract

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Abstract

A new trimeric cinchona alkaloid, the quaternary ammonium salt, α,α′,α′′-tris[O(9)-allylcinchonidinium-(4-methylphenoxymethyl)]benzene trichloride, has been synthesized and used as an efficient phase-transfer catalyst in asymmetric alkylation of N-(diphenylmethylene)glycine tert-butyl ester with very good yield (up to 97%) and high enantioselectivity (up to 98%).

Key Words

enantioselective - cinchona alkaloid - trimeric - Schiff base - α-amino acid

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References

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