title: Asymmetric synthesis of chiral dihydrothiopyrans via an organocatalytic enantioselective formal thio [3 + 3] cycloaddition reaction with binucleophilic bisketone thioethers.
abstract: An unprecedented organocatalytic highly enantioselective approach to a 3,4-dihydro-2H-thiopyran scaffold with two contiguous stereogenic centers has been implemented through a formal thio [3 + 3] cycloaddition process involving a Michael-aldol condensation cascade sequence. Notably, a new class of binucleophilic bisketone thioethers is designed for the process. Furthermore, the fine-tuning of their reactivity enables the cascade process to proceed with highly regioselectively.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University , 325 Guohe Road, Shanghai 200433, P. R. China , Department of Chemistry and Chemical Biology, University of New Mexico , Albuquerque, New Mexico 87131-0001, United States , and School of Pharmacy, East China University of Science and Technology , Shanghai 200237, P. R. China.
authors.forename: Shengzheng
authors.initials: S
authors.lastname: Wang
authors.forename: Yongqiang
authors.initials: Y
authors.lastname: Zhang
authors.forename: Guoqiang
authors.initials: G
authors.lastname: Dong
authors.forename: Shanchao
authors.initials: S
authors.lastname: Wu
authors.forename: Shiping
authors.initials: S
authors.lastname: Zhu
authors.forename: Zhenyuan
authors.initials: Z
authors.lastname: Miao
authors.forename: Jianzhong
authors.initials: J
authors.lastname: Yao
authors.forename: Hao
authors.initials: H
authors.lastname: Li
authors.forename: Jian
authors.initials: J
authors.lastname: Li
authors.forename: Wannian
authors.initials: W
authors.lastname: Zhang
authors.forename: Chunquan
authors.initials: C
authors.lastname: Sheng
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*
chemical_list: D007659:Ketones; D011714:Pyrans; D013440:Sulfides