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

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