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A method for effectively favouring 5-endo- over 5-exo-cyclisations

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
39
Issue
48
Identifiers
DOI: 10.1016/s0040-4039(98)01948-0
Keywords
  • Iodocyclisation
  • 5-Endo-Trig
  • Pyrrolidines
  • Prolines
  • Stereocontrol

Abstract

Abstract Iodocyclisation of sulfonamido-alcohol 6 proceeds by a 5-exo pathway to give amino-THFs 9 whereas the furyl derivative 10 gives the pyrrolidines 11 and 12, most likely by an alternative 5-exo mechanism, instigated by the furan ring.

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