Lewis acid mediated diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides

Shy Guey Wang; Huei Ru Tsai; Kwunmin Chen

doi:10.1016/j.tetlet.2004.05.146

Lewis acid mediated diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides

Shy Guey Wang, Huei Ru Tsai, Kwunmin Chen^*

^*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

11 引文斯高帕斯（Scopus）

摘要

Diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides was examined using allyltributyltin in the presence of various Lewis acids. The corresponding optically enriched quarternary α-hydroxy carbonyls were obtained in reasonable to excellent material yields (51-95%) and with practical levels of stereoselectivity (up to >95% de) when a stoichiometric amount of Sn(OTf)₂ was used. The stereochemical induction is discussed.

原文	英語
頁（從 - 到）	6183-6185
頁數	3
期刊	Tetrahedron Letters
卷	45
發行號	32
DOIs	https://doi.org/10.1016/j.tetlet.2004.05.146
出版狀態	已發佈 - 2004 8月 2

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

存取文件

10.1016/j.tetlet.2004.05.146

其它文件與鏈接

CCDC 247167: Experimental Crystal Structure Determination
Wang, S. (Creator), Tsai, H. R. (Creator) & Chen, K. (Creator), Unknown Publisher, 2004
DOI: 10.5517/cc8964w, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc8964w&sid=DataCite
資料集: Dataset
CCDC 247166: Experimental Crystal Structure Determination
Wang, S. (Creator), Tsai, H. R. (Creator) & Chen, K. (Creator), Unknown Publisher, 2004
DOI: 10.5517/cc8963v, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc8963v&sid=DataCite
資料集: Dataset

引用此

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title = "Lewis acid mediated diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides",

abstract = "Diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides was examined using allyltributyltin in the presence of various Lewis acids. The corresponding optically enriched quarternary α-hydroxy carbonyls were obtained in reasonable to excellent material yields (51-95%) and with practical levels of stereoselectivity (up to >95% de) when a stoichiometric amount of Sn(OTf)2 was used. The stereochemical induction is discussed.",

keywords = "Allylation",

author = "Wang, {Shy Guey} and Tsai, {Huei Ru} and Kwunmin Chen",

note = "Funding Information: This work was supported by the National Science Council of the Republic of China (NSC 92-2113-M-003-017 and NSC 92-2751-B-001-014-Y) and the National Taiwan Normal University (ORD 91-2). The X-ray crystal data were collected and processed by Taipei Instrumentation Center, College of Science, National Taiwan University and National Taiwan Normal University are gratefully acknowledged.",

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doi = "10.1016/j.tetlet.2004.05.146",

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volume = "45",

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T1 - Lewis acid mediated diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides

AU - Wang, Shy Guey

AU - Tsai, Huei Ru

AU - Chen, Kwunmin

N1 - Funding Information: This work was supported by the National Science Council of the Republic of China (NSC 92-2113-M-003-017 and NSC 92-2751-B-001-014-Y) and the National Taiwan Normal University (ORD 91-2). The X-ray crystal data were collected and processed by Taipei Instrumentation Center, College of Science, National Taiwan University and National Taiwan Normal University are gratefully acknowledged.

PY - 2004/8/2

Y1 - 2004/8/2

N2 - Diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides was examined using allyltributyltin in the presence of various Lewis acids. The corresponding optically enriched quarternary α-hydroxy carbonyls were obtained in reasonable to excellent material yields (51-95%) and with practical levels of stereoselectivity (up to >95% de) when a stoichiometric amount of Sn(OTf)2 was used. The stereochemical induction is discussed.

AB - Diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides was examined using allyltributyltin in the presence of various Lewis acids. The corresponding optically enriched quarternary α-hydroxy carbonyls were obtained in reasonable to excellent material yields (51-95%) and with practical levels of stereoselectivity (up to >95% de) when a stoichiometric amount of Sn(OTf)2 was used. The stereochemical induction is discussed.

KW - Allylation

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SP - 6183

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

Lewis acid mediated diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 247167: Experimental Crystal Structure Determination

CCDC 247166: Experimental Crystal Structure Determination

引用此