Science of Synthesis

Hatakeyama, S., Science of Synthesis: Asymmetric Organocatalysis, (2012) 1, 680.

Aromatic and aliphatic aldehydes can be enantioselectively transformed into the corresponding Morita–Baylis–Hillman 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 Morita–Baylis–Hillman reactions between aldehydes and enones to take place.