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