THE SYNTHESIS OF BRIDGED-RING CARBOCYCLES AND HETEROCYCLES VIA PALLADIUM CATALYZED REGIOSPECIFIC CYCLIZATION REACTIONS

R GRIGG*, [No Value] SANTHAKUMAR, Seshadri SRIDHARAN, P STEVENSON, A TEASDALE, M THORNTONPETT, T WORAKUN

*Corresponding author for this work

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Abstract

A catalyst system comprising 10 mol % (Pd(OAc) and 20 mol % PPh3 effects the cyclisation of aryl halides onto proximate alkenes via 5-, 6-, and 7-exo-trig, and 7-endo-trig processes giving a variety of bridged-ring carbo- and hetero-cycles in excellent yield. Double bond isomerisation in the product is rarely encountered and may be suppressed by the addition of Tl(1) salts. One example of diastereospecific bis-cyclisation is given and the crystal structure of 1-aza-2-sulphonyl-3,4-benzobicyclo[3.2.1]nona-6-ene is reported.

Original languageEnglish
Pages (from-to)9703-9720
Number of pages18
JournalTetrahedron
Volume47
Issue number46
Publication statusPublished - 25 Nov 1991

Keywords

  • PALLADIUM CATALYSIS
  • BRIDGED-RING CYCLIZATION
  • METAL-PROMOTED CYCLIZATION
  • ANION CAPTURE PROCESSES
  • POLYENE CYCLIZATIONS
  • CRYSTAL-STRUCTURE
  • SILVER-NITRATE
  • ARYLATION
  • VINYLATION
  • COMPLEXES
  • HALIDES
  • ALKENES

Cite this

GRIGG, R., SANTHAKUMAR, N. V., SRIDHARAN, S., STEVENSON, P., TEASDALE, A., THORNTONPETT, M., & WORAKUN, T. (1991). THE SYNTHESIS OF BRIDGED-RING CARBOCYCLES AND HETEROCYCLES VIA PALLADIUM CATALYZED REGIOSPECIFIC CYCLIZATION REACTIONS. Tetrahedron, 47(46), 9703-9720.