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Synthesis of Physiologically Potent β-Amino Alcohols

Abstract We have established practical protocols to the stereoselective synthesis of SYN- and ANTI-β-amino alcohols via the electrophile-promoted intramolecular amination of trichloroacetimidates derived from allylic and homoallylic alcohols. Stereoselective total synthesis of natural products conta...

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Bibliographic Details
Published in:Synlett 2004-08, Vol.2004 (10), p.1673-1685
Main Authors: Lee, Hee-Seung, Kang, Sung Ho
Format: Article
Language:English
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Summary:Abstract We have established practical protocols to the stereoselective synthesis of SYN- and ANTI-β-amino alcohols via the electrophile-promoted intramolecular amination of trichloroacetimidates derived from allylic and homoallylic alcohols. Stereoselective total synthesis of natural products containing β-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
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2004-829578