Pt(II) or Ag(I) salt catalyzed cycloisomerizations and tandem cycloadditions forming functionalized azacyclic arrays.
[reaction: see text] Cyclic ene-N-p-toluenesulfonamides tethered to an electron-deficient alkyne undergo cycloisomerizations readily under the influence of catalytic Pt(II) salts (PtCl2 or [dppbPtmu-OH]2(BF4)2) or AgOTf. Yields for this process range from 47% to 99%. The resulting functionalized 2-azahydrindans can be reacted further using the Diels-Alder reaction. Tandem cycloisomerization-cycloaddition reactions in one pot generate highly functionalized 1-azadecalin ring systems in a highly stereocontrolled manner.
Harrison
Tyler J
TJ
Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, B.C., Canada, V6T 1Z1.
Dake
Gregory R
GR
D000480:Alkynes / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010984:Platinum / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D001372:Aza Compounds; D006571:Heterocyclic Compounds; D009942:Organometallic Compounds; D012834:Silver; D010984:Platinum