From Cyclopropene to Housane Derivatives Via Intramolecular Cyclopropanation DOI Creative Commons

Darío Coto,

David Suárez‐García,

Sergio Mata

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(46)

Опубликована: Июль 12, 2024

Abstract The synthesis of housane derivatives from cyclopropenes is described. Under rhodium(II) catalysis, cyclopropenylvinyl carbinols can regioselectively generate a carbene intermediate which undergoes an intramolecular cyclopropanation to form housane, skeleton with similar ring strain as the cyclopropene precursor. procedure shows remarkable broad scope and efficiency. Moreover, method served prepare man‐made housane‐containing terpene derivatives, are not accessible by Nature.

Язык: Английский

Three-dimensional saturated C(sp3)-rich bioisosteres for benzene DOI
Jet Tsien, Chao Hu, Rohan R. Merchant

и другие.

Nature Reviews Chemistry, Год журнала: 2024, Номер 8(8), С. 605 - 627

Опубликована: Июль 9, 2024

Язык: Английский

Процитировано

45

(Bio)isosteres of ortho- and meta-substituted benzenes DOI Creative Commons
H Erik Diepers, Johannes C. L. Walker

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 859 - 890

Опубликована: Апрель 19, 2024

Saturated bioisosteres of substituted benzenes offer opportunities to fine-tune the properties drug candidates in development. Bioisosteres

Язык: Английский

Процитировано

10

Facile Synthesis of Housanes by an Unexpected Strategy DOI
Yanyao Liu,

Somanea Tranin,

Yu‐Che Chang

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Фев. 17, 2025

Rigid bicyclic hydrocarbons have emerged as important building blocks in the drug discovery industry. Despite progress this general area, bicyclo[2.1.0]pentanes (housanes) are an understudied class of molecules. Herein we report unconventional synthesis borylated housanes. Our method features a broad scope and high diastereoselectivities versatile intermediates. The route involves strain-release diboration bicyclo[1.1.0]butane intramolecular deborylative alkylation. versatility bridgehead boronic ester was demonstrated several functionalizations. Lastly, mechanism reaction investigated, unusual stereospecific diastereoselective ring expansion uncovered.

Язык: Английский

Процитировано

2

Synthesis of Cyclobutanes and Cyclobutenes by Strain-Release-Driven Ring-Opening of Bicyclo[1.1.0]butanes DOI

Xuan Zhan,

Heng-Xian He,

Quanxin Peng

и другие.

Synthesis, Год журнала: 2024, Номер 56(24), С. 3829 - 3848

Опубликована: Авг. 23, 2024

Abstract Cyclobutanes and cyclobutenes exhibit intriguing structures demonstrate significant biological activities diverse synthetic applications. This review aims to summarize recent progress in strain-release-driven ring-opening reactions of bicyclo[1.1.0]butanes (BCBs) synthesize these four-membered carbon rings. It outlines the strategies, regio- stereoselectivity, scope reactions, mechanistic implications catalytic process, providing a supplementary perspective existing reviews. 1 Introduction 2 Thermally Driven Nucleophilic Ring-Opening 3 Rearrangement Isomerization Reaction 4 Light-Driven 5 Transition-Metal/Lewis Acid Catalyzed 6 Conclusion Outlook

Язык: Английский

Процитировано

8

Stereoselective Synthesis of Highly Functionalized Bicyclo[2.1.0]pentanes by Sequential [2 + 1] and [2 + 2] Cycloadditions DOI Creative Commons
Brockton Keen,

Christina Cong,

Alberto Castanedo

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 10, 2025

This study describes a method for the stereoselective synthesis of highly functionalized bicyclo[2.1.0]pentanes (housanes). The approach utilizes two-step sequence, silver- or gold-catalyzed cyclopropenation alkynes followed by an intermolecular [2 + 2] photocycloaddition reaction with electron-deficient alkenes. is established aryldiazoacetates. A regioselective cycloaddition cyclopropane was developed using blue LED irradiation, commercially available photocatalyst as triplet-sensitizer, and low temperature (−40 °C). diastereoselective, when enantioenriched cyclopropenes are used, it proceeds enantioretention.

Язык: Английский

Процитировано

1

From Cyclopropene to Housane Derivatives Via Intramolecular Cyclopropanation DOI Creative Commons

Darío Coto,

David Suárez‐García,

Sergio Mata

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(46)

Опубликована: Июль 12, 2024

Abstract The synthesis of housane derivatives from cyclopropenes is described. Under rhodium(II) catalysis, cyclopropenylvinyl carbinols can regioselectively generate a carbene intermediate which undergoes an intramolecular cyclopropanation to form housane, skeleton with similar ring strain as the cyclopropene precursor. procedure shows remarkable broad scope and efficiency. Moreover, method served prepare man‐made housane‐containing terpene derivatives, are not accessible by Nature.

Язык: Английский

Процитировано

4

Blue Light-Induced Diazo Cross-Coupling: Synthesis of Allyldiazo Compounds through Reshuffling of Functionalities DOI Creative Commons
Jiabao Tian, Jiahao Ling, Yanan Wang

и другие.

Chemical Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

In this paper, we describe a new type of cross-coupling between simple diazo and vinyldiazo compounds that gives access to unusual allyldiazo products. Blue light discriminates two towards free carbene formation, triggering sequential cyclopropenation, (3+2) cycloaddition ring opening rearrangement processes. This strategy involves an overall reshuffle functionality olefinic carbons with extrusion nitrogen. Mechanistic studies including 15N-labelling experiment demonstrate the products derives from compounds, while reagents are selectively decomposed via energy transfer thioxanthone photocatalyst. The obtained can be efficiently converted into synthetically useful structures such as 1,3-dienes, gem-difluoro-1,4-diene, hydrazine, dihydropyrazole, pyridazine, bicyclobutane.

Язык: Английский

Процитировано

0

Advances in the Synthetic Utility of Difluorocarbene Generated from TMSCF3 (Ruppert‐Prakash Reagent) and Its Derivatives DOI Open Access
Jagadeesh Krishnan,

Kaja Sahib,

Keerthana G. Nair

и другие.

The Chemical Record, Год журнала: 2025, Номер unknown

Опубликована: Март 12, 2025

Abstract Organofluorine compounds are of pivotal significance particularly, in drug and agrochemical industries different strategies have been designed for their synthesis. The last two decades witnessed the emergence difluorocarbene as an efficient synthetic tool, providing easy access to organofluorine compounds. This review summarises reactions generated from Ruppert‐Prakash reagent (TMSCF 3 ) its derivatives TMSCF 2 Cl Br. Among various fluorination techniques available, chemistry offers a cost effective procedure, opening avenue large number details developments utility derivatives, till date.

Язык: Английский

Процитировано

0

Strain-Release-Driven Alder–Ene Reaction of Bicyclo[1.1.0]butanes with β-Fluoroalkyl-α,β-Unsaturated Ketones DOI
Wenjie Xu, Zhiyi Zhang, Hao Wu

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 18, 2025

The Alder-ene reaction of the C-C bond in bicyclo[1.1.0]butanes would provide a unique and efficient synthesis route for cyclobutene frameworks. Herein, we report regio- diastereoselective with β-fluoroalkyl-α,β-unsaturated ketones, giving wide variety cyclobutenes two contiguous centers diene products. features atoms step economies exhibits broad substrate scope. Several downstream transformations these were performed.

Язык: Английский

Процитировано

0

Palladium-Catalyzed Trans-Selective Synthesis of Spirocyclic Cyclobutanes Using α,α-Dialkylcrotyl- and Allylhydrazones DOI

Isaiah K. Eckart-Frank,

Sidney M. Wilkerson‐Hill

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(33), С. 18591 - 18597

Опубликована: Авг. 8, 2023

Herein, we demonstrate the use of E/Z mixtures α,α-disubstituted crotylhydrazones to obtain spirocyclic vinylcyclobutanes in a diastereoselective fashion. We show 24 examples 1,1-insertion/4-exo-trig tandem process produce these motifs. Additionally, alkylidene cyclobutanes can be obtained by using allylated hydrazones (11 examples). In this study, that aryl migrating group has dramatic impact on course reaction. Specifically, allylic C-H insertion products good yields bromoenones as reaction partners. When Pd(0) is used with no or alkenyl bromide, an intramolecular cyclopropanation takes place afford [2.1.0]-bicycles.

Язык: Английский

Процитировано

4