Diastereoselective Baylis-Hillman reaction using N-glyoxyloyl camphorpyrazolidinone as an electrophile: Synthesis of optically pure 2-hydroxy-3-methylene succinic acid derivative

Jia Fu Pan; Kwunmin Chen

doi:10.1016/j.tetlet.2004.02.001

Diastereoselective Baylis-Hillman reaction using N-glyoxyloyl camphorpyrazolidinone as an electrophile: Synthesis of optically pure 2-hydroxy-3-methylene succinic acid derivative

Jia Fu Pan
, 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

28 引文斯高帕斯（Scopus）

摘要

The camphorpyrazolidinone derived N-glyoxylate was efficiently prepared and used as an electrophile in the Baylis-Hillman reaction under classical DABCO catalyzed conditions. The corresponding 2-hydroxy-3-methylene succinic acid derivative was generally obtained with excellent diastereoselectivity and moderate chemical yields (51-75%).

原文	英語
頁（從 - 到）	2541-2543
頁數	3
期刊	Tetrahedron Letters
卷	45
發行號	12
DOIs	https://doi.org/10.1016/j.tetlet.2004.02.001
出版狀態	已發佈 - 2004 3月 15

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

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10.1016/j.tetlet.2004.02.001

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@article{c9866b2eb641428da89857d084801546,

title = "Diastereoselective Baylis-Hillman reaction using N-glyoxyloyl camphorpyrazolidinone as an electrophile: Synthesis of optically pure 2-hydroxy-3-methylene succinic acid derivative",

abstract = "The camphorpyrazolidinone derived N-glyoxylate was efficiently prepared and used as an electrophile in the Baylis-Hillman reaction under classical DABCO catalyzed conditions. The corresponding 2-hydroxy-3-methylene succinic acid derivative was generally obtained with excellent diastereoselectivity and moderate chemical yields (51-75\%).",

keywords = "Diasteroselective Baylis-Hillman",

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

note = "Funding Information: This work is 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 are collected and processed by Taipei Instrumentation Center, College of Science, National Taiwan University, and National Taiwan Normal University are gratefully acknowledged.",

year = "2004",

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day = "15",

doi = "10.1016/j.tetlet.2004.02.001",

language = "English",

volume = "45",

pages = "2541--2543",

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T1 - Diastereoselective Baylis-Hillman reaction using N-glyoxyloyl camphorpyrazolidinone as an electrophile

T2 - Synthesis of optically pure 2-hydroxy-3-methylene succinic acid derivative

AU - Pan, Jia Fu

AU - Chen, Kwunmin

N1 - Funding Information: This work is 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 are collected and processed by Taipei Instrumentation Center, College of Science, National Taiwan University, and National Taiwan Normal University are gratefully acknowledged.

PY - 2004/3/15

Y1 - 2004/3/15

N2 - The camphorpyrazolidinone derived N-glyoxylate was efficiently prepared and used as an electrophile in the Baylis-Hillman reaction under classical DABCO catalyzed conditions. The corresponding 2-hydroxy-3-methylene succinic acid derivative was generally obtained with excellent diastereoselectivity and moderate chemical yields (51-75%).

AB - The camphorpyrazolidinone derived N-glyoxylate was efficiently prepared and used as an electrophile in the Baylis-Hillman reaction under classical DABCO catalyzed conditions. The corresponding 2-hydroxy-3-methylene succinic acid derivative was generally obtained with excellent diastereoselectivity and moderate chemical yields (51-75%).

KW - Diasteroselective Baylis-Hillman

UR - https://www.scopus.com/pages/publications/1542302465

UR - https://www.scopus.com/pages/publications/1542302465#tab=citedBy

U2 - 10.1016/j.tetlet.2004.02.001

DO - 10.1016/j.tetlet.2004.02.001

M3 - Article

AN - SCOPUS:1542302465

SN - 0040-4039

VL - 45

SP - 2541

EP - 2543

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -

Diastereoselective Baylis-Hillman reaction using N-glyoxyloyl camphorpyrazolidinone as an electrophile: Synthesis of optically pure 2-hydroxy-3-methylene succinic acid derivative

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