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.
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1 Introduction
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2 Substrate Stereocontrol
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2.1 Diastereoselection with α-Chiral Aldehydes
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2.2 Chiral Auxiliaries Attached to Carbon
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2.2.1 Glycolaldehyde and Glyoxylic Acid Derivatives
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2.2.2 Chiral Transition-Metal π-Complexes
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2.3 Chiral Auxiliaries Attached to Nitrogen
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2.3.1 Imines from Chiral 1-Arylethylamines
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2.3.2 Imines from α-Amino Acid Derivatives
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2.3.3 Imines from Vicinal Amino Alcohols
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2.3.4 Other Imines
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2.3.5 Chiral Hydrazones and Oxime Ethers
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3 Enantioselective Stoichiometric Processes
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3.1 Chiral Modifiers in the Allyl Group
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3.2 Chiral Modifiers in the Metal Center
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4 Asymmetric Catalysis
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5 Perspectives
addition reactions - asymmetric catalysis - asymmetric synthesis - diastereoselectivity - imines
