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Synlett 2010(9): 1302-1314  
DOI: 10.1055/s-0029-1219821
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Selective Syntheses of Functionalized Cyclic β-Amino Acids via Transformation of the Ring C-C Double Bonds

Loránd Kissa, Ferenc Fülöp*a,b
a Institute of Pharmaceutical Chemistry, University or Szeged, Eötvös u. 6, 6720 Szeged, Hungary
Fax: +36(62)545705; e-Mail: fulop@pharm.u-szeged.hu;
b Research Group of Stereochemistry of the Hungarian Academy of Sciences, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary
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Publikationsverlauf

Received 20 January 2010
Publikationsdatum:
13. April 2010 (online)

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Abstract

This report provides an overview of the most important aspects of the syntheses of functionalized cyclic β-amino acids in recent years. The presentation focuses in particular on strategies involving the selective functionalization of unsaturated alicyclic β-amino acids. The limitations and shortcomings of the synthetic methods are emphasized, and the possible new challenges and developments in this field in the near future are outlined.

1 Introduction

2 Synthesis of Functionalized Cyclic β-Amino Acids via ­C-C Double Bond Transformations of the Cycloalkenes

2.1 Functionalization via Stereoselective Iodooxazination and Iodooxazoline Formation

2.2 Functionalization via Stereoselective Iodolactonization

2.3 Functionalization via Stereoselective Iodolactamization

2.4 Functionalization Involving Stereoselective Epoxidation and Regioselective Oxirane Opening

2.5 Functionalization via Selective Dihydroxylation

2.6 Functionalization via 1,3-Dipolar Cycloaddition

2.7 Other Methods Based on Functionalization of Ring C-C Double Bonds

3 Some Relevant Routes to Functionalized Cyclic β-Amino Acids other than Functionalization of Ring C-C Double Bonds

4 Conclusions

Key words

amino acids - peptides - stereoselective synthesis - enantioselectivity - enzymes