Photoactivated Formal [3 + 2] / [4+2] Cycloaddition of N‐Aryl Cyclopropyl and Cyclobutylamines DOI Creative Commons
Montserrat Zidan, Lucas F. Villela, Louis Barriault

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(44)

Published: Oct. 24, 2024

Abstract Organic transformations initiated by photochemical activation have been at the forefront of reaction discovery. In this study, we present a formal [3+2] and [4+2] cycloaddition using N ‐aryl cyclopropylamines cyclobutylamines in conjunction with α , β ‐unsaturated carbonyl systems, unveiling two distinct mechanistic pathways. The is elucidated as being guided activity an electron donor‐acceptor (EDA) complex. Simultaneously, intermolecular annulation cyclobutylanilines achieved visible‐light photoredox catalysis. These simple methodologies wide applicability, facilitating synthesis ‐arylaminocycloalkyl compounds yields ranging from good to excellent.

Language: Английский

Exploring the Reactivity of Rigid 1-Azadienes Derived from Methylene γ-Lactams. Applications to the Stereoselective Synthesis of γ-Spirolactams. DOI Creative Commons
Adrián López‐Francés, Zuriñe Serna-Burgos, Xabier del Corte

et al.

Published: March 13, 2024

A study on the reactivity of rigid 1-azadienes derived from methylene γ-lactams is reported. Through functionalization 1-amino α,β-unsaturated γ-lactam derivatives, easily available a multicomponent reaction amines, aldehydes and pyruvates it possible to in situ generate locked by core. The 4π-system those can behave as both diene dienophile species, through spontaneous cyclodimerization reaction, or exclusively dienes dienophiles if they are trapped with imines cyclopentadiene, respectively. use chiral cycloaddition cyclopentadiene leads formation γ-spirolactams bearing four stereogenic centers highly stereospecific manner, reporting first example methylene-γ-lactams synthesis spirocycles.

Language: Английский

Citations

1
Visible-light-enabled stereoselective synthesis of functionalized cyclohexylamine derivatives via [4 + 2] cycloadditions DOI Creative Commons

Yi‐Nan Lu,

Chao Che,

Guangjin Zhen

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(17), P. 6507 - 6514

Published: Jan. 1, 2024

Photocatalyzed [4 + 2] cycloaddition of benzocyclobutylamines with α-substituted vinylketones afforded benzocyclohexylamines in moderate to good yields excellent diastereoselectivities. An asymmetric version this was preliminarily investigated.

Language: Английский

Citations

1
Exploring the Reactivity of Rigid 1-Azadienes Derived from Methylene γ-Lactams. Applications to the Stereoselective Synthesis of Spiro-γ-Lactams DOI Creative Commons
Adrián López‐Francés, Zuriñe Serna-Burgos, Xabier del Corte

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9502 - 9515

Published: June 19, 2024

A study on the reactivity of rigid 1-azadienes derived from methylene γ-lactams is reported. Through functionalization 1-amino α,β-unsaturated γ-lactam derivatives, easily available a multicomponent reaction amines, aldehydes, and pyruvates, it possible to in situ generate locked by core. The 4π-electron system those can behave as both diene dienophile species through spontaneous cyclodimerization or exclusively dienes dienophiles if they are trapped with imines cyclopentadiene, respectively. use chiral cycloaddition cyclopentadiene leads formation spiro-γ-lactams bearing four stereogenic centers highly stereospecific manner, reporting first example methylene-γ-lactams synthesis spirocycles.

Language: Английский

Citations

0
Photoactivated Formal [3 + 2] / [4+2] Cycloaddition of N‐Aryl Cyclopropyl and Cyclobutylamines DOI Creative Commons
Montserrat Zidan, Lucas F. Villela, Louis Barriault

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(44)

Published: Oct. 24, 2024

Abstract Organic transformations initiated by photochemical activation have been at the forefront of reaction discovery. In this study, we present a formal [3+2] and [4+2] cycloaddition using N ‐aryl cyclopropylamines cyclobutylamines in conjunction with α , β ‐unsaturated carbonyl systems, unveiling two distinct mechanistic pathways. The is elucidated as being guided activity an electron donor‐acceptor (EDA) complex. Simultaneously, intermolecular annulation cyclobutylanilines achieved visible‐light photoredox catalysis. These simple methodologies wide applicability, facilitating synthesis ‐arylaminocycloalkyl compounds yields ranging from good to excellent.

Language: Английский

Citations

0