title: Phosphoric Acid Catalyzed Asymmetric 1,6-Conjugate Addition of Thioacetic Acid to para-Quinone Methides.
abstract: An asymmetric 1,6-conjugate addition of thioacetic acid with para-quinone methides has been developed by using chiral phosphoric acid catalysis in the presence of water. A series of sulfur-containing compounds were thus obtained in high yields with good to excellent enantioselectivities. Theoretical studies indicated that the water-bridged proton transfer is a potentially favorable reaction pathway. An unprecedented O-H⋅⋅⋅π interaction between water and the aromatic nucleus of chiral phosphoric acid was discovered to contribute significantly to the stereocontrol in the catalysis.
authors.affiliation: State key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Department of Chemistry (Tianjin), Nankai University, Tianjin, 300071, China.
authors.forename: Nan
authors.initials: N
authors.lastname: Dong
authors.affiliation: State key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Department of Chemistry (Tianjin), Nankai University, Tianjin, 300071, China.
authors.forename: Zhi-Pei
authors.initials: ZP
authors.lastname: Zhang
authors.affiliation: State key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Department of Chemistry (Tianjin), Nankai University, Tianjin, 300071, China.
authors.forename: Xiao-Song
authors.initials: XS
authors.lastname: Xue
authors.affiliation: State key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Department of Chemistry (Tianjin), Nankai University, Tianjin, 300071, China. xin_li@nankai.edu.cn.
authors.forename: Xin
authors.identifier: http://orcid.org/0000-0001-6020-9170
authors.initials: X
authors.lastname: Li
authors.affiliation: State key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Department of Chemistry (Tianjin), Nankai University, Tianjin, 300071, China.
authors.forename: Jin-Pei
authors.initials: JP
authors.lastname: Cheng
keywords: asymmetric catalysis; conjugation; organocatalysis; quinones; sulfur