Mechanisms and Origins of Regio- and Stereoselectivities in NHC-Catalyzed [3 + 3] Annulation of α-Bromoenals and 5-Aminoisoxazoles: A DFT Study DOI

Mingchao Zhang,

Zhiqiang Zhang, Yan Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10748 - 10759

Published: July 12, 2024

Density functional theory (DFT) calculations were conducted to explore the mechanisms and origins of regio- stereoselectivities underlying [3 + 3] annulation reaction between α-bromoenals 5-aminoisoxazoles with

Language: Английский

Design and Development of Carbene-Catalyzed Intramolecular Vinylogous Stetter Reaction to Access Phenanthrol Derivatives DOI

Purna Chandra Behera,

Jakkula Ramarao,

Surisetti Suresh

et al.

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

Published: March 4, 2025

The present study reveals the design and development of an N-heterocyclic carbene (NHC)-catalyzed intramolecular vinylogous Stetter reaction. This protocol enabled synthesis diverse phenanthrol derivatives naphthol-fused heterocycles in very good to excellent yields. success title reaction relies on biaryl aldehydes bearing p-quinone methide (p-QM) moiety that acts as a (1,6-conjugate) acceptor while aldehyde functional group serves acyl anion equivalent, generated situ from NHC-catalyzed umpolung. Salient features presented include atom efficiency, operational simplicity, broad substrate scope, large-scale synthesis, postsynthetic modifications.

Language: Английский

Citations

1
NHC-Catalyzed Umpolung Driven Intramolecular Cyclizations for the Generation of 3,4-Cycloheptanone Annulated Tetracyclic Indole Derivatives DOI

Purna Chandra Behera,

Bandari Anilkumar,

Jagadeesh Babu Nanubolu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8654 - 8661

Published: Oct. 7, 2024

In this Letter, we disclose the development and exploitation of umpolung reactivity N-heterocyclic carbene (NHC) organocatalysts in generating tetracyclic indole derivatives with introduction a cycloheptane ring forming event. The NHC-catalyzed intramolecular vinylogous Stetter, benzoin, formal cross-dehydrogenative coupling transformations have been executed, enabling construction 3,4-cycloheptannulated good to excellent yields. developed protocols utilize an inexpensive catalyst feature operational simplicity, atom economy, gram-scale syntheses, postsynthetic availability.

Language: Английский

Citations

4
Divergent Aromatization of α-Halobenzyl γ-Butenolides Initiated by Selective Enol Protonation to Benzo[c]fluorenones and Naphthalenes DOI

Siling Lei,

Shixuan Bu,

M. Yao

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 11067 - 11071

Published: July 23, 2024

An unprecedented divergent aromatization reaction of α-halobenzyl γ-butenolides has been described for the selective and concise synthesis highly substituted benzo higher π-extended fluorenones, 1,3-disubstituted naphthalenes depending on migration ability quaternary α-substituent. This switch from Ag

Language: Английский

Citations

3
Regioselective Decarboxylative Aromatization of Benzonorcaradienes to Substituted 1‐Acylmethyl‐4‐Arylnaphthalenes DOI Open Access

Xinchi Gong,

Shixuan Bu,

Siling Lei

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(41)

Published: July 31, 2024

Abstract Tf 2 NH‐mediated decarboxylative dearomatization reaction of benzonorcaradiene γ‐ketoacids, in situ generated by intramolecular alkenylation alkynylcyclopropane γ‐ketoacids or their tert ‐butyl esters, has been described for regioselective synthesis polyfunctionalized 1‐acylmethyl‐4‐arylnaphthalenes.

Language: Английский

Citations

2
Synthesis of Pyridin-2(1H)-imines via the Transformation of Conjugated Ynones DOI
Weiguang Yang,

Guanrong Li,

Zixin Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 9139 - 9143

Published: June 11, 2024

Conjugated ynones represent an important class of reactive species, useful synthetic intermediates, and synthons. However, the reactivity applications are usually focused on transformation mono- or dual-functional groups. Herein, we developed a straightforward synthesis pyridin-2(1H)-imines from conjugated ynones. This cascade process probably began with Michael addition 2-aminopyridines, further underwent intramolecular cyclization to generate N,O-bidentate finally reacted sulfonyl azides giving accompanying loss diazo.

Language: Английский

Citations

1
Mechanisms and Origins of Regio- and Stereoselectivities in NHC-Catalyzed [3 + 3] Annulation of α-Bromoenals and 5-Aminoisoxazoles: A DFT Study DOI

Mingchao Zhang,

Zhiqiang Zhang, Yan Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10748 - 10759

Published: July 12, 2024

Density functional theory (DFT) calculations were conducted to explore the mechanisms and origins of regio- stereoselectivities underlying [3 + 3] annulation reaction between α-bromoenals 5-aminoisoxazoles with

Language: Английский

Citations

0