Synthesis of Physiologically Potent β-Amino Alcohols

Hee-Seung Lee; Sung Ho Kang

doi:10.1055/s-2004-829578

ACCOUNT

Synthesis of Physiologically Potent β-Amino Alcohols

Hee-Seung Lee*, Sung Ho Kang*
Center for Molecular Design and Synthesis, Department of Chemistry, School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701, South Korea
Fax: +82(42)8692810; e-Mail: hee-seung_lee@kaist.ac.kr; e-Mail: shkang@kaist.ac.kr;

Abstract

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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

Key words

β-amino alcohols - natural products - trichloroacetimidate - electrophile-promoted - intramolecular amination

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