Transition metal-free [3 + 3] annulation of cyclopropanols with β-enamine esters to assemble nicotinate derivatives

A metal-free and efficient approach for the synthesis of structurally important nicotinates through 4-HO-TEMPO-mediated [3 + 3] annulation of cyclopropanols with β-enamine esters is presented. This protocol features high atom efficiency, green waste, simple operation and broad substrate scope. Moreo...

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Published inOrganic & biomolecular chemistry Vol. 21; no. 45; pp. 8984 - 8988
Main Authors Zhan, Jun-Long, Zhu, Lin, Bai, Jia-Nan, Liu, Jian-Bo, Zhang, Shi-Han, Xie, Yao-Qiang, Hu, Bo-Mei, Wang, Yang, Han, Wen-Jun
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 22.11.2023
Royal Society of Chemistry
Subjects
Atom economy
Chemical reactions
Chemical synthesis
Chemistry
Chemistry, Organic
Esters
Organic chemistry
Oxidants
Oxidizing agents
Physical Sciences
Science & Technology
Substrates
Transition metals
ALCOHOLS
(+)-COMPLANADINE
AMINATION
VINYL AZIDES
STRATEGY
TOPOISOMERASE-I
CONDENSATION
ALDEHYDES
EFFICIENT
SUBSTITUTED PYRIDINES
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Summary:A metal-free and efficient approach for the synthesis of structurally important nicotinates through 4-HO-TEMPO-mediated [3 + 3] annulation of cyclopropanols with β-enamine esters is presented. This protocol features high atom efficiency, green waste, simple operation and broad substrate scope. Moreover, the experiments of gram-scale synthesis and recovery of oxidants make this strategy more sustainable and practical. An atom-economical synthetic approach for preparing structurally important nicotinates under metal- and additive-free conditions was developed.
Bibliography:https://doi.org/10.1039/d3ob01662e
Electronic supplementary information (ESI) available. See DOI
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 14
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01662e