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^*

^*Corresponding author for this work

Department of Chemistry

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

33 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

Access to Document

10.1016/j.tet.2010.10.061

Cite this

@article{dcc3b9b4e98548b0832291610ba5d3d0,

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",

note = "Funding Information: We thank the National Science Council of the Republic of China ( NSC 99-2113-M-003-002-MY3 and NSC 99-2119-M-003-001-MY2 ) and National Taiwan Normal University ( 99T3030-5 ) for financial support of our work. Our gratitude extends to the Academic Paper Editing Clinic at NTNU, and to the National Center for High-Performance Computing for providing us with computer time and facilities. ",

year = "2010",

month = dec,

day = "24",

doi = "10.1016/j.tet.2010.10.061",

language = "English",

volume = "66",

pages = "9875--9879",

journal = "Tetrahedron",

issn = "0040-4020",

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T1 - An efficient Morita-Baylis-Hillman reaction for the synthesis of multifunctional 2-hydroxy-3-nitrobut-3-enoate derivatives

AU - Kuan, Hsuan Hao

AU - Reddy, Raju Jannapu

AU - Chen, Kwunmin

N1 - Funding Information: We thank the National Science Council of the Republic of China ( NSC 99-2113-M-003-002-MY3 and NSC 99-2119-M-003-001-MY2 ) and National Taiwan Normal University ( 99T3030-5 ) for financial support of our work. Our gratitude extends to the Academic Paper Editing Clinic at NTNU, and to the National Center for High-Performance Computing for providing us with computer time and facilities.

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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DO - 10.1016/j.tet.2010.10.061

M3 - Article

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SN - 0040-4020

VL - 66

SP - 9875

EP - 9879

JO - Tetrahedron

JF - Tetrahedron

IS - 52

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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CCDC 795732: Experimental Crystal Structure Determination

Cite this

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 795732: Experimental Crystal Structure Determination

Cite this