Ytterbium‐Catalyzed Tandem Diels–Alder/Claisen Rearrangement/Decarboxylation of Hetero‐Allenes for the Synthesis of Diarylmethanes DOI
Bin Chen, Shan Zhong,

Huilin Zhan

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 43(2), С. 199 - 204

Опубликована: Окт. 17, 2024

Comprehensive Summary A tandem Diels–Alder reaction/Claisen rearrangement/decarboxylation strategy of N ‐allenamides (or aryloxyallenes) with 3‐alkoxycarbonyl‐2‐pyrones has been developed for the efficient synthesis diarylmethanes moderate to good yields. The reaction exhibits functional group tolerance and can be applied late‐stage modifications known drug molecules. Mechanistic studies indicate that ester at 3‐position 2‐pyrones is essential, initial between proximal C=C bond crucial success reaction.

Язык: Английский

Construction of Medium-Sized Rings by Gold Catalysis DOI
Ronald L. Reyes, Tomohiro Iwai, Masaya Sawamura

и другие.

Chemical Reviews, Год журнала: 2020, Номер 121(14), С. 8926 - 8947

Опубликована: Окт. 6, 2020

Compounds having cyclic molecular frameworks are highly regarded for their abundance and diverse utilities. In particular, medium-sized carbocycles heterocycles exist in a broad spectrum of natural products, bioactive therapeutics, medicinally significant synthetic molecules. Metal-mediated methods have been developed the preparation compounds containing ring (MSR) through cyclization different classes substrates acyclic precursors. This review focuses on methodologies construction MSRs via gold catalysis. Given challenges enabling assembly sizes, we present here accounts Au-mediated giving notable 7-membered (8–11-membered ring) structures. Emphasis pathway mode selection precursors ranging from structurally biased were outlined. Reactivity patterns choice efficient Au catalysts controlling reaction performance selectivity addition to mechanistic attributes examined.

Язык: Английский

Процитировано

186

Highly Diastereo- and Enantioselective Synthesis of Tetrahydrobenzo[b]azocines via Palladium-Catalyzed [4 + 4] Cycloaddition DOI

Can Gao,

Xunhua Wang,

Jitian Liu

и другие.

ACS Catalysis, Год журнала: 2021, Номер 11(5), С. 2684 - 2690

Опубликована: Фев. 12, 2021

The construction of N-heterocyclic eight-membered rings with good regio-, stereo-, and enantioselective control remains a formidable challenge in asymmetric catalysis. Herein, we report palladium-catalyzed [4 + 4] cycloaddition anthranils γ-methylidene-δ-valerolactones the presence Et3B, delivering highly functionalized tetrahydrobenzo[b]azocine derivatives high efficiency diastereoselectivities enantioselectivities (up to 92% yield, 20:1 dr, 99% ee). Moreover, complex substrates derived from natural products (bearing different functionalities) could be well-tolerated catalytic cycloaddition. mild reaction conditions, conjunction broad substrate scope (44 examples), level stereoselectivity, provide great potential build azocine compounds simple building blocks.

Язык: Английский

Процитировано

60

Construction of bridged polycycles through dearomatization strategies DOI
Ziying Zhang,

Huabin Han,

Lele Wang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(18), С. 3960 - 3982

Опубликована: Янв. 1, 2021

Bridged polycycles are privileged molecular skeletons with wide occurrence in bioactive natural products and pharmaceuticals. Therefore, they have been the pursing target molecules of numerous chemists. The rapid convenient generation sp3-rich complex three-dimensional from simple easily available aromatics has made dearomatization a highly valuable synthetic tool for construction rigid challenging bridged rings. This review summarizes the-state-of-the-art advances strategies application ring formation, discusses their advantages limitations in-depth mechanism, highlights value total synthesis products. We wish this will provide an important reference medicinal chemists inspire further development intriguing research area.

Язык: Английский

Процитировано

57

Recent progress in the construction of eight-membered nitrogen-heterocycles DOI
Jia Li, Ziyang Dong, Changgui Zhao

и другие.

New Journal of Chemistry, Год журнала: 2024, Номер 48(11), С. 4645 - 4669

Опубликована: Янв. 1, 2024

This review summarized the progress in synthesizing eight-membered N-heterocycles over past two decades (1995–2023), inspiring synthetic chemists to develop more efficient strategies for construction of these skeletons.

Язык: Английский

Процитировано

10

Transition Metal‐Mediated Functionalization of Isoxazoles: A Review DOI
Suchithra Madhavan, Santosh Kumar Keshri, Manmohan Kapur

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2021, Номер 10(12), С. 3127 - 3165

Опубликована: Окт. 11, 2021

Abstract Isoxazoles are an important class of heterocycles with nitrogen and oxygen in a 1,2‐relationship. They find wide applications synthetic organic chemistry part several drug molecules. Since the last two decades, great progress has been achieved synthesis functionalization isoxazoles, which transition metal catalysis played pivotal role towards achieving this goal. In particular, (TM)‐mediated site‐selective functionalizations isoxazoles retain pharmacologically synthetically valuable isoxazole skeleton, highly appealing. This comprehensive review is solely dedicated to TM‐mediated wherein we have included as directing groups (DG) for TM‐catalyzed C−H reactions, direct functionalization, along cross‐coupling reactions annulation finally ring‐opening under TM‐catalysis also discussed. Also, incorporated discussions on reaction designs, their advantages limitations, mechanistic details challenges that need be addressed inspire medicinal chemists explore new arenas make use key scaffold.

Язык: Английский

Процитировано

30

Catalytic asymmetric synthesis of spirocyclobutyl oxindoles and beyond via [2+2] cycloaddition and sequential transformations DOI Creative Commons
Xia Zhong, Jiuqi Tan,

Jianglin Qiao

и другие.

Chemical Science, Год журнала: 2021, Номер 12(29), С. 9991 - 9997

Опубликована: Янв. 1, 2021

Three distinct types of chiral cyclic compounds were accessible by catalytic asymmetric synthesis spirocyclobutyl oxindoles via [2+2] cycloaddition and sequential transformations.

Язык: Английский

Процитировано

26

Construction of C–N and C–O bonds based on N-allenamide functionalization DOI
Maxime Hourtoule, Laurence Miesch

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(46), С. 9069 - 9084

Опубликована: Янв. 1, 2022

The review covers recent advances in the development of new methods involving amination and alkoxylation reactions on N -allenamides covering cycloaddition, carbofunctionalization, halogenofunctionalization as well hydrofunctionalization reactions.

Язык: Английский

Процитировано

17

Construction of Bridged Polycyclic Skeletons via Transition‐Metal Catalyzed Carbon–Carbon Bond‐Forming Reactions DOI
Ting Wu, Wenjun Tang

Chemistry - A European Journal, Год журнала: 2020, Номер 27(12), С. 3944 - 3956

Опубликована: Сен. 28, 2020

Transition-metal catalysis has become one of most important methods for constructing molecules with diverse architectures. Bridged polycyclic skeletons are often considered challenging structures in organic synthesis. This Minireview summarizes the recent progress on synthesis bridged by transition-metal-catalyzed carbon-carbon bond-forming reaction. Four main ring-forming strategies including connection via olefin or carbonyl functionality, enolate intermediacy, C-H and aryl functionality detailed some effective discussed particular emphasis reaction design mechanism.

Язык: Английский

Процитировано

26

Regiocontrollable Difunctionalization of N-Allenamines DOI Open Access
Jian Zhang,

Wanjie Liang,

Yi Yang

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(2), С. 335 - 335

Опубликована: Янв. 1, 2024

As an electron-rich diene compound, N-allenamine has received wide spread attention in recent years due to its different reaction sites and high reactivity.Efficient controllable regioselective functionalization of N-allenamines can successfully construct functionalized molecules.The research progress the field bifunctionalization is mainly discussed, mechanisms most conversions detail are discussed.

Язык: Английский

Процитировано

3

Gold-Catalyzed Tandem Annulations of Pyridylhomopropargylic Alcohols with Propargyl Alcohols DOI
Xuesong Li,

Dan-tong Xu,

Zhi‐Jie Niu

и другие.

Organic Letters, Год журнала: 2021, Номер 23(3), С. 832 - 836

Опубликована: Янв. 28, 2021

A gold-catalyzed tandem annulation of propargylic alcohols and pyridylhomopropargylic is achieved, providing an atom-economical approach to a diverse set polycyclic dihydrobenzofurans in good yields. The reaction proceeds via the 5-endo-dig cyclization/Meyer–Schuster rearrangement/Friedel–Crafts-type pathway. In this way, three C–C bonds one C–O bond form give skeleton one-pot process. Moreover, products exhibit unique optical properties, which reveal their potential application value.

Язык: Английский

Процитировано

16