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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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Published in: | Synlett 2004-08, Vol.2004 (10), p.1673-1685 |
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Main Authors: | , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that cite this one |
Online Access: | Get full text |
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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 |
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ISSN: | 0936-5214 1437-2096 |
DOI: | 10.1055/s-2004-829578 |