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Synthesis 2006(1): 1-20  
DOI: 10.1055/s-2005-921759
REVIEW
© Georg Thieme Verlag Stuttgart · New York

α,β-Dehydroamino Acids

Christoph Bonauer, Thomas Walenzyk, Burkhard König*
Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, 93040 Regensburg, Germany
Fax: +49(941)9431717; e-Mail: Burkhard.koenig@chemie.uni-regensburg.de;
Further Information

Publication History

Received 8 June 2005
Publication Date:
16 December 2005 (online)

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Abstract

Dehydroamino acids are versatile intermediates in organic synthesis and occur as frequent structural motives in natural products and biologically active compounds. This review summarizes recent work (since 1999) on the synthesis, reactions and applications of acyclic and cyclic α,β-dehydroamino acids, α,β-dehydroamino esters, and protected α,β-dehydroamino acids.

  • 1 Introduction

  • 2 Synthesis of α,β-Dehydroamino Acids

  • 2.1 By Elimination Reaction

  • 2.2 By Horner-Wadsworth-Emmons and Wittig Reactions

  • 2.3 Erlenmeyer Synthesis and Ring-Opening of Oxazolones

  • 2.4 α,β-Dehydroamino Acids from Nitroalkanes

  • 2.5 Schöllkopf Formylamino-Methylenation

  • 2.6 Synthesis of Cyclic α,β-Dehydroamino Acids

  • 3 Reactions of α,β-Dehydroamino Acids and Esters

  • 3.1 Halogenation

  • 3.2 Nucleophilic Addition

  • 3.3 Radical Addition Reactions

  • 3.4 Sonogashira Coupling Reaction

  • 3.5 Suzuki Coupling Reactions

  • 3.6 Ring-Closing Metathesis (RCM)

  • 3.7 Cycloadditions

  • 3.8 Epoxidation

  • 3.9 Hydrogenation

  • 4 Examples of α,β-Dehydroamino Acids in Natural Products

  • 4.1 β-Lactam Antibiotics

  • 4.2 Lantibiotics

  • 4.3 Azinomycins

  • 4.4 Cyclic α,β-Dehydropeptides

  • 5 Structures of α,β-Dehydroamino Acids and Peptides

  • 6 Conclusions

Key words

amino acids - peptides - α,β-dehydroamino acids - natural products - alkenes

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The more acidic 3-(CO2Et)carbazole gives the β-substituted alanine derivative in 93% yield.