title: Lewis base assisted Brønsted base catalysis: direct regioselective asymmetric vinylogous alkylation of allylic sulfones.
abstract: A Lewis base assisted Brønsted base catalysis (LBABB) strategy is applied for direct asymmetric vinylogous alkylation of allylic sulfones with Morita-Baylis-Hillman (MBH) carbonates, in which a strong Brønsted base, tert-butoxy anion, generated in situ from a tertiary amine catalyst and MBH carbonate, is crucial in activating unstabilized nucleophiles. The γ-regioselective alkylation products were obtained with good to excellent enantiomeric excess values when catalyzed by a modified cinchona alkaloid.
authors: Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, PR China.
authors: Lin
authors: L
authors: Jiang
authors: Qian
authors: Q
authors: Lei
authors: Xin
authors: X
authors: Huang
authors: Hai-Lei
authors: HL
authors: Cui
authors: Xue
authors: X
authors: Zhou
authors: Ying-Chun
authors: YC
authors: Chen
mesh_terms: D000478:Alkylation; D000498:Allyl Compounds / Q000138:chemical synthesis*; D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002930:Cinchona Alkaloids / Q000737:chemistry; D058115:Lewis Bases / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry; D055553:Prescription Drugs / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D002254:Carbonates; D002930:Cinchona Alkaloids; D058115:Lewis Bases; D010087:Oxides; D055553:Prescription Drugs; D013450:Sulfones; C052893:tert-butoxy