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
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