Environment-friendly organic synthesis using bismuth compounds. Bismuth triflate catalyzed synthesis of substituted 3,4-dihydro-2H-1-benzopyrans

Mai P. Nguyen, Joshua N. Arnold, Katherine E. Peterson, Ram S. Mohan

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

A highly catalytic method for the synthesis of dihydrobenzopyrans from salicylaldehydes has been developed. An extension of this method to the synthesis of a pyrano[2,3,b]benzopyran has also been achieved. Bi(OTf) 3•xH 2O (1 < x < 4) (0.1 mol%) smoothly catalyzes the condensation of substituted salicylaldehydes with 2,2-dimethoxypropane to give the corresponding substituted 3,4-dihydro-2H-1- benzopyrans as a mixture of diastereomers (9:1) in moderate yields. The relative configuration of the methoxy groups in the two diastereomers was established by NOE experiments. The advantages of this method include the use of an easy to handle, inexpensive and relatively non-toxic catalyst.

Original languageEnglish (US)
Pages (from-to)9369-9371
Number of pages3
JournalTetrahedron Letters
Volume45
Issue number51
DOIs
StatePublished - Dec 13 2004
Externally publishedYes

Bibliographical note

Funding Information:
We gratefully acknowledge funding from the National Science Foundation (RUI grant # 0350216). R.S.M. is also indebted to The Camille Henry Dreyfus foundation for a Henry Dreyfus Teacher Scholar award.

Keywords

  • Bismuth and compounds
  • Bismuth triflate
  • Dihydrobenzopyrans
  • Green chemistry

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