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Synlett 2006(16): 2517-2533  
DOI: 10.1055/s-2006-951468
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Enantiomerically Pure 1-Amino-2-phenylcycloalkanecarboxylic Acids (c n Phe)

Marta Lasa, Carlos Cativiela*
Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza - CSIC, 50009 Zaragoza, Spain
Fax: +34(976)761210; e-Mail: cativiela@unizar.es;
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Publication History

Received 30 March 2006
Publication Date:
22 September 2006 (online)

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Abstract

Constrained amino acids have become very important tools for modern drug discovery research. Phenylalanine is an ­appropriate residue for study, due to its participation in active site recognition. The series of 1-amino-2-phenylcycloalkanecarboxylic acids - c n Phe - constitutes an attractive family of constrained ­analogues of phenylalanine that can provide different orientations of the phenyl moiety. All stereoisomers of this series, from the ­cyclopropane to the cyclohexane members, are available in enantio­merically pure form.

1 Introduction

2 Synthesis of Enantiomerically Pure c n Phe Surrogates

2.1 Synthesis of All Stereoisomers of 1-Amino-2-phenylcyclopropanecarboxylic Acid (c3Phe)

2.2 Synthesis of All Stereoisomers of 1-Amino-2-phenyl­cyclobutanecarboxylic Acid (c4Phe)

2.3 Synthesis of All Stereoisomers of 1-Amino-2-phenylcyclopentanecarboxylic Acid (c5Phe)

2.4 Synthesis of All Stereoisomers of 1-Amino-2-phenylcyclohexanecarboxylic Acid (c6Phe)

3 Conclusion

Key words

amino acids - asymmetric synthesis - enantiomeric resolution - peptides