An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile

Jia Fu Pan; Uppala Venkatesham; Kwunmin Chen

doi:10.1016/j.tetlet.2004.10.121

An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile

Jia Fu Pan, Uppala Venkatesham, Kwunmin Chen

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

8 引文斯高帕斯（Scopus）

摘要

The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.

原文	英語
頁（從 - 到）	9345-9347
頁數	3
期刊	Tetrahedron Letters
卷	45
發行號	51
DOIs	https://doi.org/10.1016/j.tetlet.2004.10.121
出版狀態	已發佈 - 2004 12月 13

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

存取文件

10.1016/j.tetlet.2004.10.121

其它文件與鏈接

CCDC 259647: Experimental Crystal Structure Determination
Pan, J. (Creator), Venkatesham, U. (Creator) & Chen, K. (Creator), Unknown Publisher, 2005
DOI: 10.5517/cc8q5qv, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc8q5qv&sid=DataCite
資料集: Dataset
CCDC 259646: Experimental Crystal Structure Determination
Pan, J. (Creator), Venkatesham, U. (Creator) & Chen, K. (Creator), Unknown Publisher, 2005
DOI: 10.5517/cc8q5pt, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc8q5pt&sid=DataCite
資料集: Dataset

引用此

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title = "An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile",

abstract = "The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.",

keywords = "Diastereoselective, Glyoxylate-ene reaction, Stereogenic center",

author = "Pan, {Jia Fu} and Uppala Venkatesham and Kwunmin Chen",

note = "Funding Information: This work was supported by the National Science Council of the Republic of China and the National Taiwan Normal University (NSC 92-2113-M-003-017 and ORD 93-C). 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. Our gratitude also goes to the Academic Paper Editing Clinic, NTNU. ",

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AU - Pan, Jia Fu

AU - Venkatesham, Uppala

AU - Chen, Kwunmin

N1 - Funding Information: This work was supported by the National Science Council of the Republic of China and the National Taiwan Normal University (NSC 92-2113-M-003-017 and ORD 93-C). 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. Our gratitude also goes to the Academic Paper Editing Clinic, NTNU.

PY - 2004/12/13

Y1 - 2004/12/13

N2 - The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.

AB - The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.

KW - Diastereoselective

KW - Glyoxylate-ene reaction

KW - Stereogenic center

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An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 259647: Experimental Crystal Structure Determination

CCDC 259646: Experimental Crystal Structure Determination

引用此