Iron-Catalyzed Three-Component Reactions of Cyclopropanols with Alkenes and N-Heteroarenes via Ring-Opening and C–H Functionalization DOI
Jie Yang, Shuang Wu, Ying Chu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 13, 2025

An iron-catalyzed ring-opening multicomponent reaction of cyclopropyl alcohols with alkenes and N-heteroarenes involving aryl C(sp2)-H functionalization was developed. This protocol facilitates the regioselective introduction both β-carbonyl moiety an N-heteroarene group across C═C bond alkene, thus allowing a straightforward, efficient, facile access to 5-heteroarene ketones. In this process, strategy relies on alkyl radical formation from alcohols, addition bonds, heteroaryl cascades. general approach displays excellent selectivity control broad functional-group tolerance.

Language: Английский

Homo-Mannich Reaction of Cyclopropanols: A Versatile Tool for Natural Product Synthesis DOI
Tao Zhou, Qiuyuan Tan, Dan Jiang

et al.

Accounts of Chemical Research, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 17, 2025

ConspectusThe Mannich reaction, involving the nucleophilic addition of an enol(ate) intermediate to imine or iminium ion, is one most widely used synthetic methods for synthesis β-amino carbonyl compounds. Nevertheless, homo-Mannich which utilizes a homoenolate as partner and provides straightforward access valuable γ-amino compounds, remains underexplored. This can be largely attributed difficulties in generation manipulation species, despite various equivalents that have been developed. Among developed, cyclopropanol stands out due its intriguing reactivities endowed by highly strained cyclopropane. Upon activation metal, cyclopropyl alcohol prone undergo endocyclic C(sp3)–C(sp3) bond cleavage give β-keto radical intermediate, sets stage diverse range transformations. account outlines our recent progress development reaction applications natural product total synthesis. new methodology classified into two subtypes: 1) with imines ions 2) homo-Mannich-type heteroarenes. Through different ways generate ions, tandem sequential reactions C–H oxidation/homo-Mannich, Bischler–Napieralski/homo-Mannich, asymmetric allylation/homo-Mannich leading rapid assembly core scaffolds sarpagine, koumine, ibophyllidine, Aspidosperma, Melodinus, Kopsia alkaloids. Besides ring-opening indole pyrrole rings deliver schizozygane indolizidine Based on these advancements, we accomplished 29 alkaloids belonging 8 families. In this Account, present complete picture works concerning design, method development, It anticipated methodologies will find broad realm

Language: Английский

Citations

1
Enhancement of toughness and ductility to 1,2,3-triazole Click-cured elastomers via regulation of molecular network and microphase separation DOI

Shengda Zhang,

Ying He,

Shuiping Zhou

et al.

European Polymer Journal, Journal Year: 2025, Volume and Issue: unknown, P. 113835 - 113835

Published: Feb. 1, 2025

Language: Английский

Citations

0
Iron-Catalyzed Three-Component Reactions of Cyclopropanols with Alkenes and N-Heteroarenes via Ring-Opening and C–H Functionalization DOI
Jie Yang, Shuang Wu, Ying Chu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 13, 2025

An iron-catalyzed ring-opening multicomponent reaction of cyclopropyl alcohols with alkenes and N-heteroarenes involving aryl C(sp2)-H functionalization was developed. This protocol facilitates the regioselective introduction both β-carbonyl moiety an N-heteroarene group across C═C bond alkene, thus allowing a straightforward, efficient, facile access to 5-heteroarene ketones. In this process, strategy relies on alkyl radical formation from alcohols, addition bonds, heteroaryl cascades. general approach displays excellent selectivity control broad functional-group tolerance.

Language: Английский

Citations

0