Asymmetric hydroformylation of mono‐ and sesquiterpenes

László Kollár, Gábor Bóadi

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The hydroformylation of (+)‐(R)‐limonene (1), (+)‐(1R)‐isolimonene (2), camphene (3), and (+)‐β‐cedrene (4) resulted in the regiospecific formation of the corresponding linear aldehyde in the presence of homogeneous platinum and, in some cases, rhodium catalysts. The epimeric composition could be influenced slightly by optically active catalysts formed with chiral bidentate phosphines. The relative configurations of newly formed stereogenic centers were analyzed by 1H and 13C NMR. The primarily formed aldehydes of (+)‐8(15)‐cedren‐9‐ol (5) and γ‐gurjunene (6) underwent cyclization, giving a mixture of epimers of tetracyclic terpenes. Despite the moderate diastereoselection, the products are of practical importance due to their highly regioselective formation. © 1995 Wiley‐Liss, Inc.

Original languageEnglish
Pages (from-to)121-127
Number of pages7
JournalChirality
Volume7
Issue number3
DOIs
Publication statusPublished - 1995

Keywords

  • cyclic formyl‐monoterpenes
  • homogeneous catalyst
  • hydroformylation
  • platinum‐phosphine‐tin(II)chloride catalyst
  • rhodium‐phosphine catalyst
  • tricyclic formyl‐sesquiterpenes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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