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

Department of Chemistry

Research output: Contribution to journal › Article

26 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

Fingerprint

Keywords

Diasteroselective Baylis-Hillman

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Pan, J. F., & Chen, K. (2004). Diastereoselective Baylis-Hillman reaction using N-glyoxyloyl camphorpyrazolidinone as an electrophile: Synthesis of optically pure 2-hydroxy-3-methylene succinic acid derivative. Tetrahedron Letters, 45(12), 2541-2543. https://doi.org/10.1016/j.tetlet.2004.02.001

@article{ca9db456f9b849b6a202964ed15918da,

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",

year = "2004",

month = mar

day = "15",

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

language = "English",

volume = "45",

pages = "2541--2543",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "12",

}

TY - JOUR

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

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 - http://www.scopus.com/inward/record.url?scp=1542302465&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=1542302465&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2004.02.001

DO - 10.1016/j.tetlet.2004.02.001

M3 - Article

AN - SCOPUS:1542302465

VL - 45

SP - 2541

EP - 2543

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 12

ER -

Access to Document

10.1016/j.tetlet.2004.02.001