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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

3 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	11802-11811
頁數	10
期刊	Journal of Organic Chemistry
卷	79
發行號	23
DOIs	https://doi.org/10.1021/jo5023266
出版狀態	已發佈 - 2014 12月 5

ASJC Scopus subject areas

有機化學

存取文件

10.1021/jo5023266

其它文件與鏈接

CCDC 1410204: Experimental Crystal Structure Determination
Lin, H.-H. (Creator), Lee, K.-Y. (Creator), Chen, Y.-A. (Creator), Liu, C.-F. (Creator) & Yeh, M.-C. P. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc1jbfgr, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1jbfgr&sid=DataCite
資料集: Dataset
CCDC 1410199: Experimental Crystal Structure Determination
Lin, H.-H. (Creator), Lee, K.-Y. (Creator), Chen, Y.-A. (Creator), Liu, C.-F. (Creator) & Yeh, M.-C. P. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc1jbf9l, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1jbf9l&sid=DataCite
資料集: Dataset
CCDC 1410203: Experimental Crystal Structure Determination
Lin, H.-H. (Creator), Lee, K.-Y. (Creator), Chen, Y.-A. (Creator), Liu, C.-F. (Creator) & Yeh, M.-C. P. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc1jbffq, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1jbffq&sid=DataCite
資料集: Dataset

引用此

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 等.
於: Journal of Organic Chemistry, 卷 79, 編號 23, 05.12.2014, p. 11802-11811.

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

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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",

pages = "11802--11811",

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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SN - 0022-3263

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JO - Journal of Organic Chemistry

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IS - 23

ER -

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1410204: Experimental Crystal Structure Determination

CCDC 1410199: Experimental Crystal Structure Determination

CCDC 1410203: Experimental Crystal Structure Determination

引用此

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