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Synthesis 2009(10): 1725-1731  
DOI: 10.1055/s-0028-1088121
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of β-Branched Phenylalanine Derivatives via Chelate-Claisen Rearrangement

Christian Quirin, Uli Kazmaier*
Institut für Organische Chemie, Universität des Saarlandes, Geb. C4.2, 66123 Saarbrücken, Germany
Fax: +49(681)3022409; e-Mail: u.kazmaier@mx.uni-saarland.de;
Further Information

Publication History

Received 20 November 2008
Publication Date:
14 April 2009 (online)

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Abstract

Ester enolate Claisen rearrangement of chelated N-protected chiral amino acid cinnamyl esters results in the formation of substituted phenylalanine derivatives with unsaturated side chains in good yields and with a high degree of chirality transfer.

Key words

amino acids - chelates - esters - rearrangements - stereoselective synthesis

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