title: Squaramide-catalysed enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes.
abstract: A highly enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes catalysed by a chiral squaramide organocatalyst has been described. This organocatalytic reaction at an extremely low catalyst loading (0.2 mol%) furnished synthetically useful β-nitro sulfides in excellent yields with good diastereoselectivities and high enantioselectivities (up to 94 : 6 dr, 95% ee). In addition, the catalytic reaction can be performed on a 10 gram scale, and facile transformation into taurine derivative is also presented.
authors: School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China.
authors: Wen
authors: W
authors: Yang
authors: Da-Ming
authors: DM
authors: Du
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003503:Cyclobutanes / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000475:Alkenes; D003503:Cyclobutanes; D013438:Sulfhydryl Compounds; C005732:thioacetic acid