Abstract
Carbohydrates contain a high density of functional and stereochemical information in one molecular unit. They have been exploited as enantiopure starting materials in numerous ex-chiral pool syntheses. During the past decade, the potential of carbohydrates in terms of stereodifferentiating auxiliaries has been recognised. Glycosylamines proved to be efficient auxiliaries in stereoselective Strecker syntheses of α-amino nitriles and Ugi reactions yielding α-amino acid amides. Mannich-reactions of glycosyl imines with silyl ketene acetals resulted in the formation of β-amino acid derivatives with high diastereoselectivity. N-Glycosyl imines unfold their high potential in stereoselective reactions, in particular, in Mannich-Michael reaction sequences with 2-silyloxy-butadiene derivatives furnishing 2-substituted piperidinone derivatives with high asymmetric induction. On the basis of this efficient stereodifferentiation on glycosyl imines a number of alkaloids of the piperidine, indolizine, quinazoline, and decahydro-quinoline series have been synthesised in enantiomerically pure form. The N-glycosyl auxiliary has been demonstrated to control stereoselective protonation of enolates, for example, in alternative formation of cis-annulated perhydro-quinoline alkaloids typical for toxins of Dendrobates pumilio or trans-annulated analogues characteristic for toxins from Dendrobates histrionicus. Derivatives of amino sugars have been also investigated as components of enantioselective catalysts, e.g. palladium(0)-catalysed allylation reactions, allylic oxidation processes and Strecker syntheses.
Keywords: Amino Sugars, Glycosylamines, enantioselective catalysts, allylic oxidation processes
Current Organic Chemistry
Title: Amino Sugars and Glycosylamines as Tools in Stereoselective Synthesis
Volume: 8 Issue: 18
Author(s): S. Knauer, B. Kranke, L. Krause and H. Kunz
Affiliation:
Keywords: Amino Sugars, Glycosylamines, enantioselective catalysts, allylic oxidation processes
Abstract: Carbohydrates contain a high density of functional and stereochemical information in one molecular unit. They have been exploited as enantiopure starting materials in numerous ex-chiral pool syntheses. During the past decade, the potential of carbohydrates in terms of stereodifferentiating auxiliaries has been recognised. Glycosylamines proved to be efficient auxiliaries in stereoselective Strecker syntheses of α-amino nitriles and Ugi reactions yielding α-amino acid amides. Mannich-reactions of glycosyl imines with silyl ketene acetals resulted in the formation of β-amino acid derivatives with high diastereoselectivity. N-Glycosyl imines unfold their high potential in stereoselective reactions, in particular, in Mannich-Michael reaction sequences with 2-silyloxy-butadiene derivatives furnishing 2-substituted piperidinone derivatives with high asymmetric induction. On the basis of this efficient stereodifferentiation on glycosyl imines a number of alkaloids of the piperidine, indolizine, quinazoline, and decahydro-quinoline series have been synthesised in enantiomerically pure form. The N-glycosyl auxiliary has been demonstrated to control stereoselective protonation of enolates, for example, in alternative formation of cis-annulated perhydro-quinoline alkaloids typical for toxins of Dendrobates pumilio or trans-annulated analogues characteristic for toxins from Dendrobates histrionicus. Derivatives of amino sugars have been also investigated as components of enantioselective catalysts, e.g. palladium(0)-catalysed allylation reactions, allylic oxidation processes and Strecker syntheses.
Export Options
About this article
Cite this article as:
Knauer S., Kranke B., Krause L. and Kunz H., Amino Sugars and Glycosylamines as Tools in Stereoselective Synthesis, Current Organic Chemistry 2004; 8 (18) . https://dx.doi.org/10.2174/1385272043369485
DOI https://dx.doi.org/10.2174/1385272043369485 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |

- Author Guidelines
- Bentham Author Support Services (BASS)
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements