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Synthesis 2007(2): 159-186
DOI: 10.1055/s-2006-958957
DOI: 10.1055/s-2006-958957
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Recent Advances in Stereoselective Syntheses Using N-Acylimines
Further Information
Received
27 September 2006
Publication Date:
21 December 2006 (online)
Publication History
Publication Date:
21 December 2006 (online)
Abstract
The electron-withdrawing aptitude displayed by the acyl group makes N-acylamines very attractive substrates in many processes aimed at the preparation of amino derivatives. The remarkable electrophilicity of N-acylimines can be profitably used to overcome reactivity troubles often observed using N-alkylimines and N-arylimines. The presence of a polar acyl moiety on the nitrogen atom is particularly effective in stereoselective reactions were electrostatic interactions play a major role in determining the facial preference for the nucleophilic attack. Utilization of alkoxycarbonyl groups (e.g. Boc or Cbz) as activating N-acyl substituents allows one to obtain the final amino derivative in a protected form that can be readily cleaved under mild conditions. In this review, several synthetic applications of N-acylimines in stereoselective reactions that have appeared in the literature since 1990 are discussed.
1 Introduction
2 Preparation of N-Acylimines
3 Nucleophilic Additions to N-Acylimines
3.1 Reaction with Organometallic Reagents and Related Carbanions
3.1.1 Linear N-Acylimines
3.1.2 Cyclic N-Acylimines
3.2 Reaction with Enolate Anions
3.2.1 Nitroalkanes: The Aza-Henry Reaction
3.2.2 1,3-Dicarbonyls
3.2.3 Carbonyls and Related Derivatives
3.2.4 Carboxylic Acid Derivatives
3.3 Reaction with Aromatic Compounds
3.4 Reaction with Heteronucleophiles
4 Cycloaddition Reactions
5 Conclusion
Key words
amines - asymmetric synthesis - catalysis - imines - nucleophilic addition
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