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

Keywords

Diasteroselective Baylis-Hillman

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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

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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%).",

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