An efficient Morita-Baylis-Hillman reaction for the synthesis of multifunctional 2-hydroxy-3-nitrobut-3-enoate derivatives

Hsuan Hao Kuan; Raju Jannapu Reddy; Kwunmin Chen

doi:10.1016/j.tet.2010.10.061

An efficient Morita-Baylis-Hillman reaction for the synthesis of multifunctional 2-hydroxy-3-nitrobut-3-enoate derivatives

Hsuan Hao Kuan, Raju Jannapu Reddy, Kwunmin Chen

Department of Chemistry

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

32 Citations (Scopus)

Abstract

An efficient thiourea promoted MBH reaction of various conjugated nitroalkenes with ethyl glyoxylate was developed. The desired multifunctional products, 2-hydroxy-3-nitro-4-aryl/alkylbut-3-enoate derivatives were obtained in good to high chemical yields (56-92%) with DMAP (20 mol %) under solvent-free conditions or imidazole (100 mol %) in the presence of water.

Original language	English
Pages (from-to)	9875-9879
Number of pages	5
Journal	Tetrahedron
Volume	66
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2010.10.061
Publication status	Published - 2010 Dec 24

Keywords

Aqueous media
Morita-Baylis-Hillman reaction
Nitroalkenes
Organocatalysis
Thiourea

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "An efficient Morita-Baylis-Hillman reaction for the synthesis of multifunctional 2-hydroxy-3-nitrobut-3-enoate derivatives",

abstract = "An efficient thiourea promoted MBH reaction of various conjugated nitroalkenes with ethyl glyoxylate was developed. The desired multifunctional products, 2-hydroxy-3-nitro-4-aryl/alkylbut-3-enoate derivatives were obtained in good to high chemical yields (56-92%) with DMAP (20 mol %) under solvent-free conditions or imidazole (100 mol %) in the presence of water.",

keywords = "Aqueous media, Morita-Baylis-Hillman reaction, Nitroalkenes, Organocatalysis, Thiourea",

author = "Kuan, {Hsuan Hao} and Reddy, {Raju Jannapu} and Kwunmin Chen",

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AU - Reddy, Raju Jannapu

AU - Chen, Kwunmin

PY - 2010/12/24

Y1 - 2010/12/24

N2 - An efficient thiourea promoted MBH reaction of various conjugated nitroalkenes with ethyl glyoxylate was developed. The desired multifunctional products, 2-hydroxy-3-nitro-4-aryl/alkylbut-3-enoate derivatives were obtained in good to high chemical yields (56-92%) with DMAP (20 mol %) under solvent-free conditions or imidazole (100 mol %) in the presence of water.

AB - An efficient thiourea promoted MBH reaction of various conjugated nitroalkenes with ethyl glyoxylate was developed. The desired multifunctional products, 2-hydroxy-3-nitro-4-aryl/alkylbut-3-enoate derivatives were obtained in good to high chemical yields (56-92%) with DMAP (20 mol %) under solvent-free conditions or imidazole (100 mol %) in the presence of water.

KW - Aqueous media

KW - Morita-Baylis-Hillman reaction

KW - Nitroalkenes

KW - Organocatalysis

KW - Thiourea

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