title: Organocatalyzed Asymmetric 1,6-Conjugate Addition of para-Quinone Methides with Dicyanoolefins.
abstract: A chiral thiourea catalyzed asymmetric 1,6-conjugate addition of para-quinone methides with dicyanoolefins has been developed. The reaction provided an efficient approach to the synthesis of chiral diarylmethine skeletons in good yields (up to 99% yield) with high diastereo- and enantioselectivity (>20:1 dr and up to 99.5:0.5 er), also on a gram scale. The preliminary mechanistic study showed that the remote stereocontrol was achieved through intermolecular hydrogen-bond interaction between the chiral thiourea catalyst and the para-quinone methides directly for the first time.
authors.affiliation: State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University , Nanjing, 210009, P. R. China.
authors.forename: Xuanyi
authors.initials: X
authors.lastname: Li
authors.affiliation: State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University , Nanjing, 210009, P. R. China.
authors.forename: Xiuyan
authors.initials: X
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University , Nanjing, 210009, P. R. China.
authors.forename: Weiwei
authors.initials: W
authors.lastname: Wei
authors.affiliation: State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University , Nanjing, 210009, P. R. China.
authors.forename: Aijun
authors.initials: A
authors.lastname: Lin
authors.affiliation: State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University , Nanjing, 210009, P. R. China.
authors.forename: Hequan
authors.initials: H
authors.lastname: Yao
mesh_terms: D002384:Catalysis; D003516:Cycloparaffins / Q000737:chemistry*; D006860:Hydrogen Bonding; D045563:Indolequinones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry
chemical_list: D003516:Cycloparaffins; D045563:Indolequinones; C068040:quinone methide; D013890:Thiourea