title: Allylsamarium Bromide-Mediated Cascade Cyclization of Homoallylic Esters. Synthesis of 2-(2-Hydroxyalkyl)cyclopropanols and 2-(2-Hydroxyethyl)bicyclo[2.1.1]hexan-1-ols.
abstract: In continuation of our previous study on the intramolecular reductive coupling of simple homoallylic esters promoted by allylSmBr/HMPA/H2O, which afforded a facile synthesis of 2-(2-hydroxyalkyl)cyclopropanols, here we report the reductive cascade cyclization of but-3-enyl but-3-enoates mediated by allylSmBr/HMPA/CuCl2·2H2O, in which the two C═C bonds were successively coupled to allow the construction of the structurally interesting bridged bicyclic tertiary alcohols. Thus, the 2-(2-hydroxyethyl)bicyclo[2.1.1]hexan-1-ols were prepared in moderate to good yields with excellent diastereoselectivity.
authors.affiliation: †Department of Chemistry, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People's Republic of China.
authors.forename: Mengmeng
authors.initials: M
authors.lastname: Shen
authors.affiliation: †Department of Chemistry, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People's Republic of China.
authors.forename: Yawei
authors.initials: Y
authors.lastname: Tu
authors.affiliation: †Department of Chemistry, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People's Republic of China.
authors.forename: Guanqun
authors.initials: G
authors.lastname: Xie
authors.affiliation: †Department of Chemistry, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People's Republic of China.
authors.forename: Qingsheng
authors.initials: Q
authors.lastname: Niu
authors.affiliation: †Department of Chemistry, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People's Republic of China.
authors.forename: Hui
authors.initials: H
authors.lastname: Mao
authors.affiliation: †Department of Chemistry, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People's Republic of China.
authors.forename: Tingting
authors.initials: T
authors.lastname: Xie
authors.affiliation: ‡Department of Chemistry, Lehigh University, Bethlehem, Pennsylvania 18015, United States.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Flowers
authors.affiliation: †Department of Chemistry, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People's Republic of China.
authors.forename: Xin
authors.initials: X
authors.lastname: Lv
authors.affiliation: †Department of Chemistry, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People's Republic of China.
authors.forename: Xiaoxia
authors.initials: X
authors.lastname: Wang
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D004952:Esters / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D012493:Samarium / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D001643:Bridged Bicyclo Compounds; D004952:Esters; D004988:Ethers, Cyclic; C043657:cyclopropanol; D012493:Samarium