title: Synthesis of cis-3-acyl-4-alkenylpyrrolidines via gold(I)-catalyzed cycloisomerization reaction of (Z)-8-aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols.
abstract: (Z)-8-Aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols were cycloisomerized to the corresponding cis-3-acyl-4-alkenylpyrrolidines when treated with a catalytic amount of Ph(3)PAuCl/AgOTf in CH(2)Cl(2). The reaction proceeded via attack of the hydroxyl group onto the gold-activated alkynes followed by [3,3]-sigmatropic rearrangement to generate cis-3-acyl-4-alkenylpyrrolidines in good yields. This transformation can be applied to the synthesis of cis- and trans-3-acyl-4-alkenylcyclopentanes from (Z)- and (E)-8-aryloct-2-en-7-yn-1-ols, respectively.
authors.affiliation: Department of Chemistry, National Taiwan Normal University, 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China. cheyeh@ntnu.edu.tw
authors.forename: Ming-Chang P
authors.initials: MC
authors.lastname: Yeh
authors.forename: Ming-Nan
authors.initials: MN
authors.lastname: Lin
authors.forename: Wei-Jong
authors.initials: WJ
authors.lastname: Chang
authors.forename: Jia-Lun
authors.initials: JL
authors.lastname: Liou
authors.forename: Ya-Fon
authors.initials: YF
authors.lastname: Shih
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D050607:Organogold Compounds / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry*
chemical_list: D000438:Alcohols; D050607:Organogold Compounds; D011759:Pyrrolidines; D014105:Tosyl Compounds