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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

28 Citations (Scopus)

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%).

Original language	English
Pages (from-to)	2541-2543
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	12
DOIs	https://doi.org/10.1016/j.tetlet.2004.02.001
Publication status	Published - 2004 Mar 15

Keywords

Diasteroselective Baylis-Hillman

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.02.001

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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",

month = mar,

day = "15",

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

language = "English",

volume = "45",

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journal = "Tetrahedron Letters",

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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

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

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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

Abstract

Keywords

ASJC Scopus subject areas

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