Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives

Shu Mei Yang; Ganapuram Madhusudhan Reddy; Meng Hsien Liu; Tzu Ping Wang; Jhen Kuei Yu; Wenwei Lin

doi:10.1021/acs.joc.6b02526

Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives

Shu Mei Yang, Ganapuram Madhusudhan Reddy, Meng Hsien Liu, Tzu Ping Wang, Jhen Kuei Yu, 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

21 引文斯高帕斯（Scopus）

摘要

A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.

原文	英語
頁（從 - 到）	781-789
頁數	9
期刊	Journal of Organic Chemistry
卷	82
發行號	1
DOIs	https://doi.org/10.1021/acs.joc.6b02526
出版狀態	已發佈 - 2017 1月 6

ASJC Scopus subject areas

有機化學

存取文件

10.1021/acs.joc.6b02526

其它文件與鏈接

CCDC 1485688: Experimental Crystal Structure Determination
Yang, S.-M. (Creator), Madhusudhan Reddy, G. (Contributor), Liu, M.-H. (Creator), Wang, T.-P. (Creator), Yu, J.-K. (Creator) & Lin, W. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1lvzfv, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1lvzfv&sid=DataCite
資料集: Dataset
CCDC 1037980: Experimental Crystal Structure Determination
Yang, S.-M. (Creator), Madhusudhan Reddy, G. (Contributor), Liu, M.-H. (Creator), Wang, T.-P. (Creator), Yu, J.-K. (Creator) & Lin, W. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc13v379, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc13v379&sid=DataCite
資料集: Dataset
CCDC 1401267: Experimental Crystal Structure Determination
Yang, S.-M. (Creator), Madhusudhan Reddy, G. (Contributor), Liu, M.-H. (Creator), Wang, T.-P. (Creator), Yu, J.-K. (Creator) & Lin, W. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1j145w, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1j145w&sid=DataCite
資料集: Dataset

引用此

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abstract = "A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.",

author = "Yang, {Shu Mei} and {Madhusudhan Reddy}, Ganapuram and Liu, {Meng Hsien} and Wang, {Tzu Ping} and Yu, {Jhen Kuei} and Wenwei Lin",

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

year = "2017",

month = jan,

day = "6",

doi = "10.1021/acs.joc.6b02526",

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T1 - Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives

AU - Yang, Shu Mei

AU - Madhusudhan Reddy, Ganapuram

AU - Liu, Meng Hsien

AU - Wang, Tzu Ping

AU - Yu, Jhen Kuei

AU - Lin, Wenwei

PY - 2017/1/6

Y1 - 2017/1/6

N2 - A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.

AB - A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.

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Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to 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 1485688: Experimental Crystal Structure Determination

CCDC 1037980: Experimental Crystal Structure Determination

CCDC 1401267: Experimental Crystal Structure Determination

引用此