Cited by Construction of enantioenriched eight-membered lactones via Pd-catalyzed asymmetric (6+2) dipolar annulation

Opportunities for the Application and Advancement of the Corey–Chaykovsky Cyclopropanation DOI

Gregory L. Beutner, David T. George

Organic Process Research & Development, Journal Year: 2022, Volume and Issue: 27(1), P. 10 - 41

Published: Dec. 21, 2022

Cyclopropanes are a common motif in many pharmaceutically relevant compounds, and methods for the synthesis of these strained rings have relevance throughout pharmaceutical development process. Among options, Corey–Chaykovsky cyclopropanation stands out due to its broad substrate scope, high functional group tolerance, mild conditions. Despite benefits, application cyclopropanes, specifically context large-scale syntheses, has been limited. In this review, scope limitations Brønsted-base-promoted with sulfur ylides will be examined. Through discussion, gaps understanding transformation highlighted promote further advancement powerful useful methodology.

Language: Английский

Citations

Palladium-Catalyzed [3 + 2] Cycloaddition of 4-Vinyl-4-butyrolactones with Ketenes Generated in Situ from Acyl Chlorides: A Method for the Synthesis of Dihydrofurans DOI

Yujie Dong, Sen Yang, Yi Tang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(10), P. 2057 - 2061

Published: March 1, 2024

In this paper, palladium-catalyzed [3 + 2] cycloaddition of 4-vinyl-4-butyrolactones with ketenes generated from easily available acyl chlorides was achieved. With Pd2(dba)3·CHCl3/XantPhos as the catalyst, reaction proceeded smoothly under mild conditions, affording a series 2,3-dihydrofurans in moderate to high yields. The scale-up and further transformations products are demonstrated, plausible mechanism is proposed well.

Language: Английский

Citations

Vinylcyclopropanes as All-Carbon 1,5-Dipoles: A Reactivity Switch for Palladium-Catalyzed (5 + 4) Cycloadditions DOI

Anaïs Scuiller,

Alexandre Karnat,

Nicolas Casaretto

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(6), P. 2332 - 2336

Published: March 4, 2021

Azonanes were prepared by a palladium-catalyzed (5 + 4) cycloaddition between activated vinylcyclopropanes and 1-azadienes. During this process, the vinylcyclopropane partner displayed an unusual reactivity behaved as all-carbon 1,5-dipole. A N,N-bidentate ligand was required to inhibit formation of thermodynamic (3 2) cycloadducts.

Language: Английский

Citations

Construction of polycyclic structures with vicinal all-carbon quaternary stereocenters via an enantioselective photoenolization/Diels–Alder reaction DOI

Min Hou, Mengmeng Xu,

Baochao Yang

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 12(21), P. 7575 - 7582

Published: Jan. 1, 2021

All-carbon quaternary stereocenters are ubiquitous in natural products and significant drug molecules. However, construction of all-carbon is a challenging project due to their congested chemical environment. And, when vicinal present one molecule, they will dramatically increase its synthetic challenge. A chiral titanium promoted enantioselective photoenolization/Diels-Alder (PEDA) reaction allows largely stereohindered tetra-substituted dienophiles interact with highly active photoenolized hydroxy-o-quinodimethanes, delivering fused or spiro polycyclic rings bearing centers excellent enantiomeric excess through one-step operation. This newly developed PEDA inspire other advances asymmetric excited-state reactions, could be used the total synthesis structurally related complex drug-like molecules for discovery.

Language: Английский

Citations

Construction of enantioenriched eight-membered lactones via Pd-catalyzed asymmetric (6+2) dipolar annulation DOI

Baocheng Wang,

Wei Yi,

Feng-Ya Xiong

et al.

Science China Chemistry, Journal Year: 2022, Volume and Issue: 65(12), P. 2437 - 2443

Published: Nov. 3, 2022

Language: Английский

Citations