Transition metal-catalyzed enantioselective hydrogenation of enamides and enamines is one of the most important methods for the preparation of optically active amines. This review describes the recent developments of highly efficient catalytic asymmetric hydrogenation of enamides, and enamines. It specifically focuses on the substrates because hydrogenation of enamides and enamines is highly dependent on the substrates although the chiral metal catalysts play a significant role.

Transition Metal-Catalyzed Enantioselective Hydrogenation of Enamines and Imines

BINOL: A Versatile Chiral Reagent

The review examines the chiral amine literature from 2000-2009 (May) concerning enantioselective and diastereoselective methods for N-acylenamide and enamine reduction, reductive amination, and imine reduction. The reaction steps for each strategy, from ketone to primary chiral amine, are clearly defined, with best methods and yields for starting material preparation and final deprotection noted. Categories of chiral amines have been defined in Section 1 to allow the reader to quickly understand whether their specific target amine falls within a difficult to synthesize, or not, structural class. Amino acids are not considered in this work.

Chiral Amine Synthesis – Recent Developments and Trends for Enamide Reduction, Reductive Amination, and Imine Reduction

Catalytic Asymmetric Synthesis of α-Amino Acids

Chiral tertiary alcohols and R-tertiary amines are important building blocks of naturally occurring and artificial biologically active molecules. Although there are catalytic asymmetric oxidation and amination reactions to access these chiral building blocks, the catalytic asymmetric addition of carbon nucleophiles to ketones and ketimines, which can simultaneously construct a carbon skeleton and tetrasubstituted stereogenic center, is synthetically more efficient (Scheme 1). Realizing the catalytic asymmetric addition to ketones and ketimines (tetrasubstituted carbon synthesis), however, is generally more challenging than addition to aldehydes or aldimines (trisubstituted carbon synthesis) for two main reasons: (1) ketones and ketimines are significantly less reactive than aldehydes and aldimines; (2) enantio-face differentiation of ketones and ketimines is more difficult due to the smaller steric and electronic differences between the two substituents on prochiral carbons. Therefore, asymmetric catalysts that promote C-C bond-formation to ketones and ketimines should have high catalyst activity and enantioselectivity.

Asymmetric Synthesis of Tertiary Alcohols and α-Tertiary Amines via Cu-Catalyzed C−C Bond Formation to Ketones and Ketimines

A highly enantioselective catalyst generated by a combination of BINOL and another ligand with Ti(OiPr)4 was found to be highly effective for the alkynylzinc addition to aromatic aldehydes with enantioselectivities as high as >99%.

Highly enantioselective alkynylzinc addition to aromatic aldehydes catalyzed by self-assembled titanium catalysts.

Enantioselective Alkynylation of Aromatic Ketones Catalyzed by Chiral Camphorsulfonamide Ligands

Titanium-catalyzed enantioselective alkynylation of aldehydes.

A series of binaphthyl-derived amino alcohols were synthesized and used as catalytic ligands in the asymmetric alkynylation of aromatic aldehydes in the presence of a dialkylzinc reagent. The alkynylation of a variety of aromatic aldehydes gave the corresponding chiral propargylic alcohols in 61–93% e.e.

Enantioselective alkynylation of aromatic aldehydes catalyzed by new chiral amino alcohol-based ligands

Highly Enantioselective Alkynylzinc Addition to Aromatic Aldehydes Catalyzed by Self-Assembled Titanium Catalysts.

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