A Regioselective [3 + 2] Cycloaddition of Alkynols and Ketones To Access Diverse 1,3-Dioxolane Scaffolds DOI
Ganesh Kumar Dhandabani,

Jeyakannu Palaniraja,

Chia-Ling Shih

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 719 - 724

Опубликована: Дек. 27, 2023

This study presents a stepwise exoselective [3 + 2] cycloaddition reaction of alkynols with ketones, leading to the synthesis 4-methylene-1,3-dioxolane derivatives. Remarkably, without any Thorpe–Ingold induced effect, cyclization was demonstrated complete regio- and chemoselectivity, which solely promoted by cesium carbonate. A wide range unactivated ketones are viable under these mild conditions, both primary tertiary compatible reactions. We have prepared diverse array highly dense exomethylene 1,3-dioxolane rings demonstrating remarkable tolerance for various functional groups.

Язык: Английский

Recent Progress in Application of Propargylic Alcohols in Organic Syntheses DOI
Fatemeh Doraghi,

Amir Mohammad Mahdavian,

Somaye Karimian

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(18), С. 2991 - 3019

Опубликована: Июль 14, 2023

Abstract Propargylic alcohols are readily available bifunctional (alkyne and hydroxyl groups) synthons, which recognize as one of the attractive synthetic feedstock in organic transformations. Especially, recent years employment these valuable molecules has frequently been observed literature. Hence, present review highlights advancements application propargylic cyclization, substitution, addition reactions.

Язык: Английский

Процитировано

16

Development of novel transition metal-catalyzed synthetic approaches for the synthesis of a dihydrobenzofuran nucleus: a review DOI Creative Commons

Rabia Ashraf,

Ameer Fawad Zahoor, Kulsoom Ghulam Ali

и другие.

RSC Advances, Год журнала: 2024, Номер 14(21), С. 14539 - 14581

Опубликована: Янв. 1, 2024

The synthesis of dihydrobenzofuran scaffolds bears pivotal significance in the field medicinal chemistry and organic synthesis. These heterocyclic hold immense prospects owing to their significant pharmaceutical applications as they are extensively employed essential precursors for constructing complex frameworks. Their versatility importance make them an interesting subject study researchers scientific community. While exploring synthesis, have unveiled various novel efficient pathways assembling core. In wake extensive data being continuously reported each year, we outlined recent updates (post 2020) on methodological accomplishments employing catalytic role several transition metals forge functionalities.

Язык: Английский

Процитировано

6

Alcohol Dehydrogenases and N‐Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β‐Disubstituted Allylic Alcohols DOI
Sergio González‐Granda, Iván Lavandera, Vicente Gotor‐Fernández

и другие.

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(25), С. 13945 - 13951

Опубликована: Март 15, 2021

The combination of gold(I) and enzyme catalysis is used in a two-step approach, including Meyer-Schuster rearrangement series readily available propargylic alcohols followed by stereoselective bioreduction the corresponding allylic ketone intermediates, to provide optically pure β,β-disubstituted alcohols. This cascade involves gold N-heterocyclic carbene an enzyme, demonstrating compatibility both catalyst types aqueous medium under mild reaction conditions. [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene][bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2 ) selective alcohol dehydrogenase (ADH-A from Rhodococcus ruber, KRED-P1-A12 or KRED-P3-G09) led synthesis active (E)-4-arylpent-3-en-2-ols good yields (65-86 %). approach was also extended various 2-hetarylpent-3-yn-2-ol, hexynol, butynol derivatives. use dehydrogenases opposite selectivity production allyl enantiomers (93->99 % ee) for broad panel substrates.

Язык: Английский

Процитировано

31

Organocatalytic asymmetric cascade bicyclization: access to chiral polycyclic bisindoles from 2-indolylmethanols and propargylic alcohols DOI
Wen-Run Zhu, Qiong Su, Xiaoyi Deng

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(7), С. 2040 - 2046

Опубликована: Янв. 1, 2024

A chiral phosphoric acid-catalyzed asymmetric bis-cyclization of α-indolyl propargylic alcohols with 2-indolylmethanols was realized.

Язык: Английский

Процитировано

5

Recent Advances in Photo-promoted Generalized C3-H Alkylation of Quinoxalin-2(1H)-ones DOI
Youpeng Zuo, Xu Bai, Cong Wang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Recent advances in the photo-promoted C3–H alkylation reaction of quinoxalin-2(1 H )-ones with different agents.

Язык: Английский

Процитировано

0

A review towards synthesis of heterocycles using propargyl alcohols and propargyl amines DOI
Amit Ranjan Pandey, Durgesh Kumar Tiwari, Aditya Prakhar

и другие.

Monatshefte für Chemie - Chemical Monthly, Год журнала: 2022, Номер 153(5-6), С. 383 - 407

Опубликована: Май 20, 2022

Язык: Английский

Процитировано

11

Bi(OTf)3-Catalyzed Alkyl-Intercepted Meyer–Schuster Rearrangement of Propargylic Alcohols for the Synthesis of 1,2,3,5-Tetrasubstituted Pentane-1,5-diones DOI
Zhihai Wang,

Yuxing Sun,

Qinglin Zhang

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(5), С. 3329 - 3340

Опубликована: Фев. 11, 2022

An alkyl intercepted Meyer-Schuster rearrangement reaction with α,β-unsaturated ketones as the electrophiles was first investigated, which provided a facile method to construct 2-methylene-pentane-1,5-diones. Then in situ generated 2-methylene-pentane-1,5-diones underwent Michael addition give diverse 2-malononitrile methyl substituted pentane-1,5-diones one-pot fashion. This transformation reliable on gram scale. The high yield, convenient experimental operation, and 100% atom economy made it valuable for construction of 1,2,3,5-tetrasubstituted pentane-1,5-dione derivatives.

Язык: Английский

Процитировано

8

Alcohol Dehydrogenases and N‐Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β‐Disubstituted Allylic Alcohols DOI
Sergio González‐Granda, Iván Lavandera, Vicente Gotor‐Fernández

и другие.

Angewandte Chemie, Год журнала: 2021, Номер 133(25), С. 14064 - 14070

Опубликована: Март 15, 2021

Abstract The combination of gold(I) and enzyme catalysis is used in a two‐step approach, including Meyer–Schuster rearrangement series readily available propargylic alcohols followed by stereoselective bioreduction the corresponding allylic ketone intermediates, to provide optically pure β,β‐disubstituted alcohols. This cascade involves gold N‐heterocyclic carbene an enzyme, demonstrating compatibility both catalyst types aqueous medium under mild reaction conditions. [1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene][bis(trifluoromethanesulfonyl)‐imide]gold(I) (IPrAuNTf 2 ) selective alcohol dehydrogenase (ADH‐A from Rhodococcus ruber , KRED‐P1‐A12 or KRED‐P3‐G09) led synthesis active ( E )‐4‐arylpent‐3‐en‐2‐ols good yields (65–86 %). approach was also extended various 2‐hetarylpent‐3‐yn‐2‐ol, hexynol, butynol derivatives. use dehydrogenases opposite selectivity production allyl enantiomers (93‐>99 % ee for broad panel substrates.

Язык: Английский

Процитировано

9

Regioselective Synthesis of Benzannulated [5,6]-Oxaspirolactones via Cu(II)-Catalyzed Cycloisomerization of 2-(5-Hydroxyalkynyl)benzoates DOI
Sagar S. Thorat,

Sagar P. Shimpi,

Pooja I. Sambherao

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(24), С. 16915 - 16933

Опубликована: Ноя. 27, 2023

Spiroketals and oxaspirolactones are widely found in biologically active natural products, serving as important structural motifs. In this study, we present a Cu(II)-catalyzed cascade cycloisomerization of 2-(5-hydroxyalkynyl)benzoates, enabling the regioselective synthesis benzannulated [5,6]-oxaspirolactones containing an isochromen-1-one moiety. This strategy offers rapid efficient approach to access diverse array [5,6]-oxaspirolactones. The methodology presented here showcases broad substrate scope, delivering good yields scalability up gram scale. structures were unequivocally confirmed through single-crystal X-ray analysis by analogy using 1H 13C{1H} NMR data.

Язык: Английский

Процитировано

3

Recent Advances in Gold(I)-Catalyzed Approaches to Three-Type Small-Molecule Scaffolds via Arylalkyne Activation DOI Creative Commons
Lu Yang,

Hongwei Su,

Yue Sun

и другие.

Molecules, Год журнала: 2022, Номер 27(24), С. 8956 - 8956

Опубликована: Дек. 15, 2022

Gold catalysts possess the advantages of water and oxygen resistance, with possibility catalyzing many novel chemical transformations, especially in syntheses small-molecule skeletons, addition to achieving rapid construction multiple bonds ring systems one step. In this feature paper, we summarize recent advances scaffolds, such as benzene, cyclopentene, furan, pyran, based on gold-catalyzed cyclization arylalkyne derivatives within last decade. We hope that review will serve a useful reference for chemists apply strategies related natural products active molecules, hopefully providing guidance exploration additional approaches.

Язык: Английский

Процитировано

5