Copper-Catalyzed Tandem Cross-Coupling/Thermally Promoted [2 + 2] Cycloaddition of 1,6-Enynes and Diazo Compounds To Assemble Methylenecyclobutane-Fused Ring System

Chen, Nuan; Zhou, Ting; Zhang, Hong; Zhu, Yuqi; Lang, Ming; Wang, Jian; Peng, Shiyong

doi:10.1021/acs.joc.1c00104

Cited by 11 publications

(1 citation statement)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A plausible reaction pathway is depicted in Scheme In the same year, the Peng and Wang group demonstrated an copper-catalyzed cascade cyclization reaction of 1,6-alkynes and diazo compounds, allowing the generation of cyclobutyric[b]dihydroindoles in moderate to excellent yields (Scheme 32). [31] This tandem protocol, which proceeded through a sequential cross-coupling/[2 + 2] cycloaddition sequences, pro-vided effective access to the methylenecyclobutanefused ring systems with high proximal-regioselectivity and diastereoselectivity. In addition, phenol-derived 1,6-enynes and thiophene-derived 1,6-enynes were compatible with the catalytic system, and the desired products were achieved under mild reaction conditions.…”

Section: Cu-catalyzed Reaction Of 16-enynesmentioning

confidence: 99%

Recent Advances in Cyclization Reactions of 1,6‐Enynes

Liu,

Xu,

Han

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

Elaborated molecular architectures, specifically those bearing one or more carbon stereocenters, stand as an important class of carbocyclic and heterocyclic frameworks because they are frequently occurring core structures in numerous natural products and biologically active pharmaceutical molecules. Over the past few decades, the development of novel and versatile synthetic approaches via cascade cyclization reactions of 1,6‐enynes for the construction of a series of fused and spiro compounds has been the focus of a great deal of research initiatives. These synthesis strategies are peculiarly fascinating in the context of the assembly of a wide array of pharmaceutical molecules, natural products, agrochemicals, and functional materials. In this review, recent developments in the transformations of 1,6‐enynes with diverse coupling reagents are summarized since 2018, which could be divided into five categories: 1) Introduction; 2) Transition metal catalyzed cyclization of 1,6‐enynes; 3) Metal‐free cyclization of 1,6‐enynes; 4) Visible‐light‐induced cyclization of 1,6‐enynes; 5) Electrocatalytic cyclization of 1,6‐enynes.

show abstract

Section: Cu-catalyzed Reaction Of 16-enynesmentioning

confidence: 99%

Recent Advances in Cyclization Reactions of 1,6‐Enynes

Liu,

Xu,

Han

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

Stereoselective Synthesis of Kalafungin Based on CuI‐Catalyzed Tandem Reactions of Arylethynes Containing an Ortho‐(1‐Hydroxyethyl) Substituent with Alkyl Diazoacetates

et al. 2021

View full text Add to dashboard Cite

An isochromene synthesis is developed utilizing a cascade reaction involving a CuI catalyzed coupling reaction between an alkyne and diazoacetate followed by allenoate isomerization and subsequent oxa‐Michael addition. The cascade sequence was also demonstrated for the synthesis of naphthalenes. Furthermore, the methodology developed herein was applied toward a stereoselective synthesis of pyranonaphthoquinone kalafungin.

show abstract

Copper‐Catalyzed Chemo‐ and Diastereoselective 1,3‐Dipolar Cycloaddition of Carbonyl Ylide and Aldehyde‐Tethered‐Cyclohexadienone to Access Polycyclic Systems

et al. 2021

Self Cite

View full text Add to dashboard Cite

A copper‐catalyzed tandem intermolecular ylide formation/intramolecular cycloaddition of diazo compounds and aldehyde‐tethered‐cyclohexadienones was reported, chemo‐ and diastereoselectively providing oxapolycyclic frameworks in moderate to excellent yields under mild conditions. This reaction creates two C−C bonds and one C−O bond with five stereocentres including two all‐carbon quaternary centres. Moreover, the late‐stage diversification of products can be realized via chemoselective substitutions.

show abstract

Copper-Catalyzed Tandem Cross-Coupling/Thermally Promoted [2 + 2] Cycloaddition of 1,6-Enynes and Diazo Compounds To Assemble Methylenecyclobutane-Fused Ring System

Cited by 11 publications

References 58 publications

Recent Advances in Cyclization Reactions of 1,6‐Enynes

Recent Advances in Cyclization Reactions of 1,6‐Enynes

Stereoselective Synthesis of Kalafungin Based on CuI‐Catalyzed Tandem Reactions of Arylethynes Containing an Ortho‐(1‐Hydroxyethyl) Substituent with Alkyl Diazoacetates

Copper‐Catalyzed Chemo‐ and Diastereoselective 1,3‐Dipolar Cycloaddition of Carbonyl Ylide and Aldehyde‐Tethered‐Cyclohexadienone to Access Polycyclic Systems

Contact Info

Product

Resources

About