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1.1.16.1 Asymmetric Amine-Catalyzed Reactions of Aldehydes

DOI: 10.1055/sos-SD-204-00330

Hatakeyama, S.Science of Synthesis: Asymmetric Organocatalysis, (20121680.

Aromatic and aliphatic aldehydes can be enantioselectively transformed into the corresponding MoritaBaylisHillman products by reactions with α,β-unsaturated esters, α,β-unsaturated ketones, and α,β-unsaturated aldehydes using chiral bifunctional amine catalysts. Such reactions can also be achieved enantioselectively using a chiral thiourea as a Brønsted acid activator, together with 1,4-diazabicyclo[2.2.2]octane or 4-(dimethylamino)pyridine. Furthermore, the combination of an imidazole-based nucleophile and an amino acid as a cocatalyst allows enantioselective MoritaBaylisHillman reactions between aldehydes and enones to take place.