title: Highly efficient asymmetric Michael addition of aldehyde to nitroolefin using perhydroindolic acid as a chiral organocatalyst.
abstract: Perhydroindolic acids, the by-products obtained in the industrial production of a trandolapril intermediate, were used as chiral organocatalysts in asymmetric Michael addition reactions of aldehydes to nitroolefins. These proline-like catalysts are unique for their rigid bicyclic structure with two H atoms attached to the bridgehead C atoms lying on the opposite side of the ring. They therefore showed high efficiency in asymmetric Michael additions of aldehydes to nitroolefins. Under the optimal conditions, excellent diastereo- and enantioselectivities (up to 99/1 dr and 98% ee) were obtained with high chemical yields for a series of aldehydes and nitroolefins using only 5 mol% catalyst loading. The methodology features easily available catalysts, high catalytic efficiency and environmentally green procedures.
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, PR China.
authors.forename: Lina
authors.initials: L
authors.lastname: Zhao
authors.forename: Jiefeng
authors.initials: J
authors.lastname: Shen
authors.forename: Delong
authors.initials: D
authors.lastname: Liu
authors.forename: Yangang
authors.initials: Y
authors.lastname: Liu
authors.forename: Wanbin
authors.initials: W
authors.lastname: Zhang
mesh_terms: D000147:Acids, Heterocyclic / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis*; D002384:Catalysis; D015394:Molecular Structure; D017672:Nitrogen Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000147:Acids, Heterocyclic; D000447:Aldehydes; D000475:Alkenes; D017672:Nitrogen Compounds