Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives

Geng Hua Chang; Chein Yi Wang; G. Madhusudhan Reddy; Yi Ling Tsai; Wenwei Lin

doi:10.1021/acs.joc.6b02041

Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives

Geng Hua Chang, Chein Yi Wang, G. Madhusudhan Reddy, Yi Ling Tsai, Wenwei Lin^*

^*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

20 引文斯高帕斯（Scopus）

摘要

An enantioselective synthesis of benzopyrano[3,4-c]pyrrolidine derivatives via organocatalyzed [3 + 2] cycloaddition has been achieved. Cinchona alkaloid-derived organocatalysts as Brønsted bases have been examined for this asymmetric cycloaddition of o-hydroxy aromatic aldimines with 3-substituted coumarins. An unexpected rearrangement of the quaternary acyl moiety in the products resulted in an in situ protection of the o-hydroxy group.

原文	英語
頁（從 - 到）	10071-10080
頁數	10
期刊	Journal of Organic Chemistry
卷	81
發行號	20
DOIs	https://doi.org/10.1021/acs.joc.6b02041
出版狀態	已發佈 - 2016 10月 21

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有機化學

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10.1021/acs.joc.6b02041

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CCDC 1495672: Experimental Crystal Structure Determination
Chang, G. (Creator), Wang, C. (Creator), Madhusudhan Reddy, R. G. (Contributor), Tsai, Y. (Creator) & Lin, W. (Creator), Unknown Publisher, 2016
DOI: 10.5517/ccdc.csd.cc1m6chp, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1m6chp&sid=DataCite
資料集: Dataset
CCDC 1495671: Experimental Crystal Structure Determination
Chang, G. (Creator), Wang, C. (Creator), Madhusudhan Reddy, R. G. (Contributor), Tsai, Y. (Creator) & Lin, W. (Creator), Unknown Publisher, 2016
DOI: 10.5517/ccdc.csd.cc1m6cgn, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1m6cgn&sid=DataCite
資料集: Dataset

引用此

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abstract = "An enantioselective synthesis of benzopyrano[3,4-c]pyrrolidine derivatives via organocatalyzed [3 + 2] cycloaddition has been achieved. Cinchona alkaloid-derived organocatalysts as Br{\o}nsted bases have been examined for this asymmetric cycloaddition of o-hydroxy aromatic aldimines with 3-substituted coumarins. An unexpected rearrangement of the quaternary acyl moiety in the products resulted in an in situ protection of the o-hydroxy group.",

author = "Chang, {Geng Hua} and Wang, {Chein Yi} and {Madhusudhan Reddy}, G. and Tsai, {Yi Ling} and Wenwei Lin",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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doi = "10.1021/acs.joc.6b02041",

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volume = "81",

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T1 - Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives

AU - Chang, Geng Hua

AU - Wang, Chein Yi

AU - Madhusudhan Reddy, G.

AU - Tsai, Yi Ling

AU - Lin, Wenwei

PY - 2016/10/21

Y1 - 2016/10/21

N2 - An enantioselective synthesis of benzopyrano[3,4-c]pyrrolidine derivatives via organocatalyzed [3 + 2] cycloaddition has been achieved. Cinchona alkaloid-derived organocatalysts as Brønsted bases have been examined for this asymmetric cycloaddition of o-hydroxy aromatic aldimines with 3-substituted coumarins. An unexpected rearrangement of the quaternary acyl moiety in the products resulted in an in situ protection of the o-hydroxy group.

AB - An enantioselective synthesis of benzopyrano[3,4-c]pyrrolidine derivatives via organocatalyzed [3 + 2] cycloaddition has been achieved. Cinchona alkaloid-derived organocatalysts as Brønsted bases have been examined for this asymmetric cycloaddition of o-hydroxy aromatic aldimines with 3-substituted coumarins. An unexpected rearrangement of the quaternary acyl moiety in the products resulted in an in situ protection of the o-hydroxy group.

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ER -

Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1495672: Experimental Crystal Structure Determination

CCDC 1495671: Experimental Crystal Structure Determination

引用此