Synthesis of 1,2-Difunctionalized Fine Chemicals through Catalytic, Enantioselective Ring-Opening Reactions of Epoxides

Christoph Schneider

doi:10.1055/s-2006-950348

REVIEW

Synthesis of 1,2-Difunctionalized Fine Chemicals through Catalytic, Enantioselective Ring-Opening Reactions of Epoxides

Christoph Schneider*
Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany
Fax: +49(341)9736599; e-Mail: schneider@chemie.uni-leipzig.de;

Abstract

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Abstract

This review summarizes the development of metal- and enzyme-catalyzed, enantioselective ring-opening reactions of meso-epoxides and racemic epoxides with various hetero and carbon nucleophiles towards the synthesis of highly enantiomerically enriched 1,2-difunctionalized fine chemicals.

1 Introduction

2 Desymmetrization of meso-Epoxides

2.1 Azide Additions

2.2 Amine Additions

2.3 Alcohol and Acid Additions

2.4 Thiol Additions

2.5 Selenol Additions

2.6 Halogen Additions

2.7 Cyanide Additions

2.8 Alkylation and Reductions

2.9 Rearrangements

2.10 Enzymatic Hydrolysis

3 Kinetic Resolution of Racemic Epoxides

3.1 With Azides

3.2 With Amines

3.3 With Alcohols

3.4 With Water (Hydrolytic Kinetic Resolution)

3.4.1 With Chemical Catalysts

3.4.2 With Enzymes

3.5 Enzyme-Catalyzed Addition of Halides and Pseudohalides to Epoxides

3.6 With Carbon Nucleophiles

4 Conclusion

Key words

asymmetric synthesis - desymmetrization - enzymes - epoxides - kinetic resolution

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