Efficient Enantioselective Michael Addition of Nitroalkenes Catalyzed by a Surfactant-Type Bifunctional Thiourea Organocatalyst in the Presence of Water

Title: Efficient Enantioselective Michael Addition of Nitroalkenes Catalyzed by a Surfactant-Type Bifunctional Thiourea Organocatalyst in the Presence of Water

Volume: 9 Issue: 1

Author(s): Jian Li, Yang Liu and Li Liu

Affiliation:

Keywords: Bifunctional thiourea, enantioselective michael addition, organocatalysts, surfactant-type, water, L-proline, amine, thiophosgene, enzymes, stereoselectivities

Abstract: New surfactant-type bifunctional thiourea organocatalysts 3 were synthesized. It was found that in the presence of 10 mol% PhCOOH, bifunctional thiourea bearing a long chain 3b in 10 mol% loading could smoothly catalyze the asymmetric Michael reaction of nitroalkenes 4 with cyclohexanone at room temperature in the presence of water, giving the desired adducts 5a-i in good yields (80 - 93%) with high diastereoselectivities (syn/anti = 95/5 - > 99/1) and enantioselectivities (up to 92% ee).

Cite this article as:

Li Jian, Liu Yang and Liu Li, Efficient Enantioselective Michael Addition of Nitroalkenes Catalyzed by a Surfactant-Type Bifunctional Thiourea Organocatalyst in the Presence of Water, Letters in Organic Chemistry 2012; 9 (1) . https://dx.doi.org/10.2174/157017812799304024