Sulfamidate Imine Derived 1-Azadienes: A New Class of Dipolarophiles in Pd-Catalyzed [3+2] Cycloadditions DOI
Mark Lautens, Alexa Torelli

Synfacts, Journal Year: 2023, Volume and Issue: 19(07), P. 0689 - 0689

Published: June 16, 2023

Key words palladium catalysis - [3+2] cycloaddition vinyl cyclopropanes

Language: Английский

Pd-Catalysed asymmetric allylic alkylation of heterocycles: a user's guide DOI
F. Richard,

Paul G. Clark,

Al Hannam

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(4), P. 1936 - 1983

Published: Jan. 1, 2024

This review analyses recent advances and strategies employed in the Pd-AAA of nucleophilic prochiral heterocycles. Each section is focused on a specific heterocycle, where optimisation data reaction scope have been carefully analysed.

Language: Английский

Citations

12
Synthesis of Bridged Bicyclic Systems peri‐Annulated to the Indole Ring: Tropane‐Fused Indoles DOI

Sergey M. Antropov,

Sofiya A. Tokmacheva,

Ирина И. Левина

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2784 - 2790

Published: April 23, 2024

Abstract Ytterbium triflate catalysed domino reaction of (3‐formyl‐4‐indolyl)‐derived donor‐acceptor cyclopropane with primary amines provides a simple approach to an unprecedented tetracyclic skeleton in which tropane system is peri ‐annulated indole core. This process involves the formation imine and its (3+2)‐cross‐cycloaddition moiety, yielding tropane‐fused core under mild conditions. These products are significant interest for pharmacology as potential hybrid molecules dual mode action.

Language: Английский

Citations

5
Catalytic Asymmetric Cycloadditions of Cyclic Sulfamidate Imines: Straightforward Access to Chiral N‐Heterocycles DOI Creative Commons

Jong‐Un Park,

Ju Hyun Kim

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 3926 - 3942

Published: July 25, 2024

Abstract Chiral N‐heterocyclic compounds are key structures in natural and pharmaceuticals, they serve as essential building blocks of functional materials. Catalytic asymmetric cycloaddition reactions represent one the most efficient synthetic strategies for constructing optically active heterocycles. Cyclic sulfamidate imines have recently come to be extensively studied widely utilized both organocatalytic transition metal‐catalyzed cycloadditions, where been shown provide various N‐fused‐heterocycles spiro‐cycles exhibiting high efficiencies with excellent stereoselectivities. This review highlights recent advancements catalytic cycloadditions cyclic stereoselective synthesis biologically sulfamidate‐containing heterocycles since 2012 while focusing on diverse reactivities mechanisms chiral induction catalysis.

Language: Английский

Citations

1
Efficient Access to Spiro[Quinazoline-Thiophen](Thi)Ones Via Acetic Acid Catalyzed [3 + 2] Annulation of Quinazolin(Thi)One Enamines with Dithianediol DOI

Jingxi Fang,

Zhentao Pan,

Yingbo Rao

et al.

Published: Jan. 1, 2024

Download This Paper Open PDF in Browser Add to My Library Share: Permalink Using these links will ensure access this page indefinitely Copy URL DOI

Language: Английский

Citations

0
Efficient access to spiro[quinazoline-thiophen](thi)ones via acetic acid mediated [3 + 2] annulation of quinazolin(thi)one enamines with dithianediol DOI

Jingxi Fang,

Zhentao Pan,

Yingbo Rao

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 138, P. 154965 - 154965

Published: Feb. 26, 2024

Language: Английский

Citations

0
Dicarbofunctionalization via C–C Bonds Cleavage DOI
Junhao Zhang,

Fujie Liu,

Shuo Ma

et al.

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Language: Английский

Citations

0
Palladium-Catalyzed (3+2) and (4+2) Cycloaddition Reactions of Sulfamidate Imine-Derived Azadienes: Synthesis of Spirocyclic Pyrrolidines and Tetrahydroquinolines DOI
Chi Bong Eric Chao, Quoc Hoang Pham, Christopher Richardson

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13744 - 13755

Published: Aug. 29, 2024

Diastereoselective Pd-catalyzed (3+2) and (4+2) cycloaddition reactions of sulfamidate imine-derived 1-azadienes with zwitterionic N-dipoles derived from 1-tosyl-2-vinylaziridine 4-vinylbenzoxazinone have been developed. These provide highly functionalized azaspirocycles featuring three contiguous stereocenters. The sulfonyl imine moiety the cycloadducts can be fully reduced to access valuable β-amino alcohols.

Language: Английский

Citations

0
Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized O-Heterocycles DOI

Liang-Chen Ren,

Min Wang, Xiao Zha

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 20, 2024

A convenient electrochemical oxidative cascade cyclization of alkenes equipped with pendant alcohols general nucleophiles was developed. Using readily available diarylmethanimine and carboxylic acids as nucleophilic sources, a broad range internal alkene terminal substrates could produce RCO2- Ar2CN-functionalized O-heterocycles in moderate to high yields without the requirement for external oxidants metals. These resulting products can subsequently be hydrolyzed yield valuable NH2- OH-functionalized tetrahydrofurans tetrahydropyranes under mild conditions. Importantly, efficient conversion secondary alcohol amines complete inversion configuration enhances methodology, enabling construction 2-aryl-3-amino tetrahydrofuran complementary diastereoselectivity.

Language: Английский

Citations

0
Palladium-Catalyzed N-Allylic Alkylation of Pyrazoles and Unactivated Vinylcyclopropanes DOI

Shao-Jie Cheng,

Xin-Li Zhang,

Zhongyue Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 20, 2024

An efficient palladium-catalyzed N-allylic alkylation of pyrazoles and unactivated vinylcyclopropanes is demonstrated, affording various N-alkyl in ≤99% yield. This protocol displays high atom economy, a broad range substrates, excellent regioselectivity stereoselectivity. Late-stage modification bioactive molecules, scaled-up reaction, divergent derivatization documented the practicability this methodology. The preliminary mechanistic investigation hinted that Pd–H species promotes ring opening cyclopropanes.

Language: Английский

Citations

0
Sulfamidate Imine Derived 1-Azadienes: A New Class of Dipolarophiles in Pd-Catalyzed [3+2] Cycloadditions DOI
Mark Lautens, Alexa Torelli

Synfacts, Journal Year: 2023, Volume and Issue: 19(07), P. 0689 - 0689

Published: June 16, 2023

Key words palladium catalysis - [3+2] cycloaddition vinyl cyclopropanes

Language: Английский

Citations

0