title: Organocatalytic sequential Michael reactions: stereoselective synthesis of multifunctionalized tetrahydroindan derivatives.
abstract: Multifunctionalized tetrahydroindan derivatives with four stereocenters were constructed via two sequential Michael reactions between cyclic γ,δ-unsaturated-β-ketoester and nitroalkenes initiated with 0.5-2 mol % of cinchona alkaloid based bifunctional organocatalysts and then with 1 equiv of tetramethylguanidine for cyclization. The desired products could be obtained in high yields (up to 99% yield) with excellent enantioselectivities (95-99% ee) as well as diastereoselectivities (up to >99:1 dr) even on a gram scale.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, P R China.
authors.forename: Peng
authors.initials: P
authors.lastname: He
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Jian
authors.initials: J
authors.lastname: Shi
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry*; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D002930:Cinchona Alkaloids; D003517:Cyclopentanes; D007189:Indans; D009574:Nitro Compounds