Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary: Efficient synthesis of highly optically active two stereoisomers

Jung Hsuan Chen; Uppala Venkatesham; Li Chen Lee; Kwunmin Chen

doi:10.1016/j.tet.2005.10.042

Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary: Efficient synthesis of highly optically active two stereoisomers

Jung Hsuan Chen, Uppala Venkatesham, Li Chen Lee, 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

19 引文斯高帕斯（Scopus）

摘要

Complementary allylation conditions were developed for the synthesis of both diastereomers of tertiary homoallylic alcohols. Treatment of camphor N-tosylpyrazolidinone derived α-ketoamides with allyltributylstannane afforded both the individual homoallylic alcohols in high optical purity (up to 98% de) when the reaction was carried out in the presence of Sn(OTf)₂ and PdCl₂, respectively. The stereochemical outcome and reversal of stereoselectivity in the reaction are proposed based on ¹³C NMR and FTIR studies.

原文	英語
頁（從 - 到）	887-893
頁數	7
期刊	Tetrahedron
卷	62
發行號	5
DOIs	https://doi.org/10.1016/j.tet.2005.10.042
出版狀態	已發佈 - 2006 1月 30

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

存取文件

10.1016/j.tet.2005.10.042

其它文件與鏈接

CCDC 284467: Experimental Crystal Structure Determination
Chen, J. (Creator), Venkatesham, U. (Creator), Lee, L. (Creator) & Chen, K. (Creator), Unknown Publisher, 2006
DOI: 10.5517/cc9k0c6, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc9k0c6&sid=DataCite
資料集: Dataset
CCDC 281390: Experimental Crystal Structure Determination
Chen, J. (Creator), Venkatesham, U. (Creator), Lee, L. (Creator) & Chen, K. (Creator), Unknown Publisher, 2006
DOI: 10.5517/cc9ft3m, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc9ft3m&sid=DataCite
資料集: Dataset
CCDC 281389: Experimental Crystal Structure Determination
Chen, J. (Creator), Venkatesham, U. (Creator), Lee, L. (Creator) & Chen, K. (Creator), Unknown Publisher, 2006
DOI: 10.5517/cc9ft2l, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc9ft2l&sid=DataCite
資料集: Dataset

引用此

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title = "Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary: Efficient synthesis of highly optically active two stereoisomers",

abstract = "Complementary allylation conditions were developed for the synthesis of both diastereomers of tertiary homoallylic alcohols. Treatment of camphor N-tosylpyrazolidinone derived α-ketoamides with allyltributylstannane afforded both the individual homoallylic alcohols in high optical purity (up to 98% de) when the reaction was carried out in the presence of Sn(OTf)2 and PdCl2, respectively. The stereochemical outcome and reversal of stereoselectivity in the reaction are proposed based on 13C NMR and FTIR studies.",

keywords = "Allylation, Chiral auxiliary, Reversal of stereoselectivity",

author = "Chen, {Jung Hsuan} and Uppala Venkatesham and Lee, {Li Chen} and Kwunmin Chen",

note = "Funding Information: This work was supported by the National Science Council of the Republic of China (NSC 94-2113-M-003-003) and the National Taiwan Normal University (ORD 93-C). The X-ray crystal data were collected and processed by National Taiwan Normal University are gratefully acknowledged. ",

year = "2006",

month = jan,

day = "30",

doi = "10.1016/j.tet.2005.10.042",

language = "English",

volume = "62",

pages = "887--893",

journal = "Tetrahedron",

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T1 - Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary

T2 - Efficient synthesis of highly optically active two stereoisomers

AU - Chen, Jung Hsuan

AU - Venkatesham, Uppala

AU - Lee, Li Chen

AU - Chen, Kwunmin

N1 - Funding Information: This work was supported by the National Science Council of the Republic of China (NSC 94-2113-M-003-003) and the National Taiwan Normal University (ORD 93-C). The X-ray crystal data were collected and processed by National Taiwan Normal University are gratefully acknowledged.

PY - 2006/1/30

Y1 - 2006/1/30

N2 - Complementary allylation conditions were developed for the synthesis of both diastereomers of tertiary homoallylic alcohols. Treatment of camphor N-tosylpyrazolidinone derived α-ketoamides with allyltributylstannane afforded both the individual homoallylic alcohols in high optical purity (up to 98% de) when the reaction was carried out in the presence of Sn(OTf)2 and PdCl2, respectively. The stereochemical outcome and reversal of stereoselectivity in the reaction are proposed based on 13C NMR and FTIR studies.

AB - Complementary allylation conditions were developed for the synthesis of both diastereomers of tertiary homoallylic alcohols. Treatment of camphor N-tosylpyrazolidinone derived α-ketoamides with allyltributylstannane afforded both the individual homoallylic alcohols in high optical purity (up to 98% de) when the reaction was carried out in the presence of Sn(OTf)2 and PdCl2, respectively. The stereochemical outcome and reversal of stereoselectivity in the reaction are proposed based on 13C NMR and FTIR studies.

KW - Allylation

KW - Chiral auxiliary

KW - Reversal of stereoselectivity

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M3 - Article

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VL - 62

SP - 887

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JO - Tetrahedron

JF - Tetrahedron

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ER -

Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary: Efficient synthesis of highly optically active two stereoisomers

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 284467: Experimental Crystal Structure Determination

CCDC 281390: Experimental Crystal Structure Determination

CCDC 281389: Experimental Crystal Structure Determination

引用此