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Novel Bifunctional Chiral Thiourea Catalyzed Highly Enantioselective aza-Henry Reaction

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journal contribution
posted on 01.05.2008 by Chungui Wang, Zhenghong Zhou, Chuchi Tang
A novel bifunctional chiral thiourea organocatalyst bearing a glycosyl scaffold and a tertiary amino group was synthesized starting from readily available alpha-d-glucose. This thiourea was proven to be an effective organocatalyst for the asymmetric aza-Henry reaction between N-Boc imines and nitromethane. The corresponding adducts were obtained in good to excellent yields with excellent enantioselectivities (up to 99.8% ee). In addition, the reaction of nitroethane also proceeded smoothly with excellent enantioselectivity, albeit with low to good diastereoselectivities.