Synthesis of medium and large cyclic amines in rhodium-catalysed reactions of aminoalkenes with H 2/CO 1

David J. Bergmann, Eva M. Campi, W. Roy Jackson, Antonio F. Patti, Dilek Saylik

Research output: Contribution to journalArticleResearchpeer-review

7 Citations (Scopus)

Abstract

Rhodium-catalysed reactions of N-benzyl- or N-alkyl-aminoalkenes (6) with H 2/CO can give cyclic amines (7) (7-13 ring size) in good to excellent yields when BIPHEPHOS is used as a ligand. Hydrogenation of the aminoalkene becomes a competing reaction for the smaller rings but can be overcome by using a H 2/CO gas ratio of 1:5. Reactions of 2-alkenyloxybenzylamines (13) gave 9-, 12- and 17-membered rings (14) in 30-40% yield, but dimer formation (16) and/or hydrogenation were competing reactions. Similar reactions of alkenylamides and ortho-alkenylanilines gave only non-cyclized amino aldehydes as products in low isolated yields.

Original languageEnglish
Pages (from-to)835-844
Number of pages10
JournalAustralian Journal of Chemistry
Volume53
Issue number10
DOIs
Publication statusPublished - 1 Dec 2000

Keywords

  • Biphepos
  • Cyclic amines
  • Rhodium catalysts

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