Synthesis of physiologically potent beta-amino alcohols

Abstract

We have established practical protocols to the stereoselective synthesis of syn- and anti-beta-amino alcohols via the electrophile-promoted intramolecular amination of trichloroacetimidates derived from allylic and homoallylic alcohols. Stereoselective total synthesis of natural products containing beta-amino alcohol functionality has been achieved by means of these methods. 1 Introduction 2 Mechanistic Considerations 3 Z-Olefinic Allylic Trichloroacetimidates 3.1 Swansonine 3.2 Castanospermine and N-Acetylneuraminic Acid 3.3 Carbapenem 4 Terminal Olefinic Homoallylic Trichloroacetimidates 4.1 Statine and Its Analogues 4.2 Anisomycin and Polyoxamic Acid 4.3 Furanomycin 4.4 Azasugars 5 Z-Olefinic Homoallylic Trichloroacetimidates 6 Miscellaneous Substrates 6.1 Trisubstituted Olefins 6.2 1,1-Disubstituted Olefins 6.3 E-Olefinic Allylic Trichloroacetimidates 7 Summary