Synthesis of multisubstituted 2-(dihydrofuran-2(3H)-ylidene)acetates via intramolecular carboalkoxylation by platinum-olefin catalyst system

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

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

(Chemical Equation Presented) The cyclization of 6-(1-alkoxyethyl)hex-2- ynoates in the presence of a platinum-olefin catalyst system gave the corresponding multisubstituted 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 led to the Z isomer, while the phenyl ester gave the E isomer.

Original languageEnglish
Pages (from-to)309-312
Number of pages4
JournalOrganic letters
Volume10
Issue number2
DOIs
Publication statusPublished - 2008 Jan 17

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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