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

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

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

3 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 language	English
Pages (from-to)	11802-11811
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	79
Issue number	23
DOIs	https://doi.org/10.1021/jo5023266
Publication status	Published - 2014 Dec 5

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo5023266

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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. / Lin, Hsin Hui; Lee, Kuan Yi; Chen, Yin An et al.
In: Journal of Organic Chemistry, Vol. 79, No. 23, 05.12.2014, p. 11802-11811.

Research output: Contribution to journal › Article › peer-review

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title = "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",

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.",

author = "Lin, {Hsin Hui} and Lee, {Kuan Yi} and Chen, {Yin An} and Liu, {Chi Fan} and Yeh, {Ming Chang P.}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

month = dec,

day = "5",

doi = "10.1021/jo5023266",

language = "English",

volume = "79",

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journal = "Journal of Organic Chemistry",

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AU - Lin, Hsin Hui

AU - Lee, Kuan Yi

AU - Chen, Yin An

AU - Liu, Chi Fan

AU - Yeh, Ming Chang P.

PY - 2014/12/5

Y1 - 2014/12/5

N2 - 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.

AB - 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.

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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

Abstract

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CCDC 1410203: Experimental Crystal Structure Determination

CCDC 1024456: Experimental Crystal Structure Determination

CCDC 1410199: Experimental Crystal Structure Determination

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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

Abstract

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Datasets

CCDC 1410203: Experimental Crystal Structure Determination

CCDC 1024456: Experimental Crystal Structure Determination

CCDC 1410199: Experimental Crystal Structure Determination

Cite this

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