Environment friendly organic synthesis using bismuth compounds. An efficient method for carbonyl-ene reactions catalyzed by bismuth triflate

Erin D. Anderson, Justin J. Ernat, Mai P. Nguyen, Ann C. Palma, Ram S. Mohan

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

Bismuth triflate (0.1 mol %) is a highly efficient catalyst for the cyclization of citronellal 1, a reaction that yields a ratio of 80:20 of isopulegol 2 and neoisopulegol 3. This methodology has also been extended to the synthesis of substituted piperidines. The bismuth triflate catalyzed ene reaction of aldehyde 4 gives a 70:30 mixture of piperidines 5 and 6. The advantages of these methods include the use of a highly efficient catalyst that is relatively nontoxic, cheap and easy to handle.

Original languageEnglish (US)
Pages (from-to)7747-7750
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number45
DOIs
StatePublished - Nov 7 2005
Externally publishedYes

Bibliographical note

Funding Information:
We are grateful to the National Science Foundation for an RUI (Research at An Undergraduate Institution) grant. We also wish to acknowledge Research Corporation for a Cottrell College Science Award. R.M. wishes to thank The Camille and Henry Dreyfus Foundation for a Henry Dreyfus Teacher Scholar Award.

Keywords

  • Bismuth and compounds
  • Carbonyl-ene reaction
  • Cyclizations
  • Lewis acids

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