Oxidative free radical reactions of enamino esters

Che Ping Chuang; Yi Lung Wu

doi:10.1016/j.tet.2003.12.035

Oxidative free radical reactions of enamino esters

Che Ping Chuang
, Yi Lung Wu

Department of Chemistry

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

54 Citations (Scopus)

Abstract

Oxidative free radical reactions of enamino esters are described. Electrophilic carbon-centered radicals produced by the cerium(IV) ammonium nitrate (CAN) oxidation of β-dicarbonyl compounds undergo efficient addition to the C-C double bond of enamino esters. This CAN mediated free radical reaction between enamino esters and β-dicarbonyl compounds provides a novel method for the synthesis of highly substituted pyrroles. The direct CAN oxidation of β-enaminocinnamates gave the dimerization products effectively.

Original language	English
Pages (from-to)	1841-1847
Number of pages	7
Journal	Tetrahedron
Volume	60
Issue number	8
DOIs	https://doi.org/10.1016/j.tet.2003.12.035
Publication status	Published - 2004 Feb 16

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2003.12.035

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title = "Oxidative free radical reactions of enamino esters",

abstract = "Oxidative free radical reactions of enamino esters are described. Electrophilic carbon-centered radicals produced by the cerium(IV) ammonium nitrate (CAN) oxidation of β-dicarbonyl compounds undergo efficient addition to the C-C double bond of enamino esters. This CAN mediated free radical reaction between enamino esters and β-dicarbonyl compounds provides a novel method for the synthesis of highly substituted pyrroles. The direct CAN oxidation of β-enaminocinnamates gave the dimerization products effectively.",

author = "Chuang, \{Che Ping\} and Wu, \{Yi Lung\}",

note = "Funding Information: We are grateful to the National Science Council of the ROC for financial support (Grant No. NSC-91-2113-M-006-008). ",

year = "2004",

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doi = "10.1016/j.tet.2003.12.035",

language = "English",

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TY - JOUR

T1 - Oxidative free radical reactions of enamino esters

AU - Chuang, Che Ping

AU - Wu, Yi Lung

N1 - Funding Information: We are grateful to the National Science Council of the ROC for financial support (Grant No. NSC-91-2113-M-006-008).

PY - 2004/2/16

Y1 - 2004/2/16

N2 - Oxidative free radical reactions of enamino esters are described. Electrophilic carbon-centered radicals produced by the cerium(IV) ammonium nitrate (CAN) oxidation of β-dicarbonyl compounds undergo efficient addition to the C-C double bond of enamino esters. This CAN mediated free radical reaction between enamino esters and β-dicarbonyl compounds provides a novel method for the synthesis of highly substituted pyrroles. The direct CAN oxidation of β-enaminocinnamates gave the dimerization products effectively.

AB - Oxidative free radical reactions of enamino esters are described. Electrophilic carbon-centered radicals produced by the cerium(IV) ammonium nitrate (CAN) oxidation of β-dicarbonyl compounds undergo efficient addition to the C-C double bond of enamino esters. This CAN mediated free radical reaction between enamino esters and β-dicarbonyl compounds provides a novel method for the synthesis of highly substituted pyrroles. The direct CAN oxidation of β-enaminocinnamates gave the dimerization products effectively.

UR - https://www.scopus.com/pages/publications/0842289092

UR - https://www.scopus.com/pages/publications/0842289092#tab=citedBy

U2 - 10.1016/j.tet.2003.12.035

DO - 10.1016/j.tet.2003.12.035

M3 - Article

AN - SCOPUS:0842289092

SN - 0040-4020

VL - 60

SP - 1841

EP - 1847

JO - Tetrahedron

JF - Tetrahedron

IS - 8

ER -

Oxidative free radical reactions of enamino esters

Abstract

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