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.
(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.
Yeh
Ming-Chang P
MC
Department of Chemistry, National Taiwan Normal University, 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China. cheyeh@ntnu.edu.tw
Lin
Ming-Nan
MN
Chang
Wei-Jong
WJ
Liou
Jia-Lun
JL
Shih
Ya-Fon
YF
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*
D000438:Alcohols; D050607:Organogold Compounds; D011759:Pyrrolidines; D014105:Tosyl Compounds