Stereochemical control by an ester group or olefin ligand in platinum-catalyzed carboalkoxylation of 6-(1-alkoxyethoxy)-hex-2-ynoates

Itaru Nakamura, Ching Siew Chan, Toshiharu Araki, Masahiro Terada, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

The cyclization of 6-(1-alkoxyethoxy)hex-2-ynoantes in the presence of the platinum-olefin catalyst system gave the corresponding multisubsti-tuted 2- [dihydrofuran-2(3H)-ylidene]acetates in good to high yields. The Z/E selectivity is controlled by the electronic property of the ester group; the 2,2,2-trichloroethyl ester yielded the Z isomer, while the phenyl ester gave the E isomer. Moreover, we found that the Z/E selectivities in the reaction of phenyl esters 1h, 1n, and 1o were controlled by the olefin ligand. For example, the platinum-catalyzed reaction of lh using 1,5-hexadiene as the olefin ligand gave E-2h as the major product, while that using 1,5-cyclo-octadiene produced mainly the Z isomer.

Original languageEnglish
Pages (from-to)1089-1100
Number of pages12
JournalAdvanced Synthesis and Catalysis
Volume351
Issue number7-8
DOIs
Publication statusPublished - 2009 May 1

Keywords

  • Alkene ligands
  • Alkynes
  • Cyclization
  • Het-erocycles
  • Platinum
  • Stereoselectivity

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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