Diastereoselective synthesis of 2-arylmethylene-6-hydroxyspiro[4.5]deca-7-ones via FeCl3·6H2O-catalyzed spiroannulation/hydride transfer of 6-(5-arylpent-4-yn-1-yl)-7-oxabicyclo[4.1.0]heptan-2-ols

Hsin Hui Lin, Kuan Yi Lee, Yin An Chen, Chi Fan Liu, Ming Chang P. Yeh

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

In the presence of a catalytic amount of FeCl3·6H2O, 6-(5-arylpent-4-yn-1-yl)-7-oxabicyclo[4.1.0]heptan-2-ols underwent attack of the pendant acetylene at the iron-activated oxirane to give a vinylic carbocation. Hydride transfer from the carbinol carbon to the newly formed cation center furnished 2-arylmethylene-6-hydroxyspiro[4.5]deca-7-ones in excellent stereoselectivity and good yields.

Original languageEnglish
Pages (from-to)11802-11811
Number of pages10
JournalJournal of Organic Chemistry
Volume79
Issue number23
DOIs
Publication statusPublished - 2014 Dec 5

ASJC Scopus subject areas

  • Organic Chemistry

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