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

doi:10.1021/jo5023266

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

J Org Chem. 2014 Dec 5;79(23):11802-11. doi: 10.1021/jo5023266. Epub 2014 Nov 20.

Authors

Hsin-Hui Lin¹, Kuan-Yi Lee, Yin-An Chen, Chi-Fan Liu, Ming-Chang P Yeh

Affiliation

¹ Department of Chemistry, National Taiwan Normal University , 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China.

PMID: 25398015
DOI: 10.1021/jo5023266

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.