Novel Chiral Thiourea Derived from Hydroquinine and L-Phenylglycinol: An Effective Catalyst for Enantio- and Diastereoselective Aza-Henry Reaction

A series of chiral thiourea bearing multiple H-bond donors derived from hydroquinine has been reported. The aza-Henry reaction of isatin-derived ketimines and long-chain nitro-alkanes catalyzed by these chiral thioureas can achieve high enantioselectivity (78-99% ee) and excellent diastereoselectivity (up to 99:1). This work is the first report on long-chain nitroalkanes as substrates with excellent diastereoselectivity in metal-free catalytic systems.

Automated summary

A series of chiral thiourea compounds with multiple H-bond donors derived from hydroquinine have been reported. The aza-Henry reaction of isatin-derived ketimines and long-chain nitro-alkanes catalyzed by these chiral thioureas shows high enantioselectivity and excellent diastereoselectivity. This work represents the first report on long-chain nitroalkanes as substrates with excellent diastereoselectivity in metal-free catalytic systems.