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Synthesis 2005(17): 2815-2829  
DOI: 10.1055/s-2005-872181
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Addition of Allylic Nucleophiles to Imino Compounds

Hui Dinga,, Gregory K. Friestad*b
a Department of Chemistry, University of Vermont, Burlington, VT 05405, USA
b Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA
Fax: +1(319)3351270; e-Mail: gregory-friestad@uiowa.edu;
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Publication History

Received 25 April 2005
Publication Date:
17 August 2005 (online)

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Abstract

Approaches to controlling C=N facial selectivity in allylic addition to imino compounds are reviewed. Stereocontrol methods involving chiral substrates, auxiliaries, reagents, and catalysts are discussed in the context of recent examples.

  • 1 Introduction

  • 2 Substrate Stereocontrol

  • 2.1 Diastereoselection with α-Chiral Aldehydes

  • 2.2 Chiral Auxiliaries Attached to Carbon

  • 2.2.1 Glycolaldehyde and Glyoxylic Acid Derivatives

  • 2.2.2 Chiral Transition-Metal π-Complexes

  • 2.3 Chiral Auxiliaries Attached to Nitrogen

  • 2.3.1 Imines from Chiral 1-Arylethylamines

  • 2.3.2 Imines from α-Amino Acid Derivatives

  • 2.3.3 Imines from Vicinal Amino Alcohols

  • 2.3.4 Other Imines

  • 2.3.5 Chiral Hydrazones and Oxime Ethers

  • 3 Enantioselective Stoichiometric Processes

  • 3.1 Chiral Modifiers in the Allyl Group

  • 3.2 Chiral Modifiers in the Metal Center

  • 4 Asymmetric Catalysis

  • 5 Perspectives

Key words

addition reactions - asymmetric catalysis - asymmetric synthesis - diastereoselectivity - imines

1

Current address: Department of Chemistry, Johns Hopkins University, Baltimore, MD, USA