Brønsted acid-catalyzed synthesis of spirocyclobutanes via heteroannulation of vinyloxyphenylbicyclobutanes with water DOI

Masaharu Takatsuki,

Hiroshi Aoyama, Mitsuhiro Arisawa

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(23), P. 4727 - 4731

Published: Jan. 1, 2024

We report a perchloric acid-catalyzed heteroannulation for the synthesis of spirocyclobutanes using vinyloxyphenylbicyclobutanes with water.

Language: Английский

Strain-release transformations of bicyclo[1.1.0]butanes and [1.1.1]propellanes DOI Creative Commons
Qianqian Hu, Jie Chen, Yang Yang

et al.

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 9, P. 100070 - 100070

Published: Feb. 28, 2024

Bicyclo[1.1.0]butanes (BCBs) and [1.1.1]propellanes (tricyclo[1.1.1.01,3]pentanes, TCPs) are structurally unique compounds with different chemical properties. Strain-release driven reactions have emerged as an atom- step-economic strategy for the organic synthesis. Using this strategy, a variety of functional ring molecules been efficiently synthesized, including various cyclobutane molecules, bicyclo[2.1.1]hexanes, bicyclo[1.1.1]pentanes, others. More specifically, these strain release-driven include aspects nucleophilic addition, radical electrophilic or transition metal catalysis. This review will discuss recent developments in strain-release transformations bicyclo[1.1.0]butanes [1.1.1]propellanes.

Language: Английский

Citations

28
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

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(24), P. 3829 - 3848

Published: Aug. 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

Language: Английский

Citations

8
Spiro[3.3]heptane as a Saturated Benzene Bioisostere** DOI Creative Commons

Kateryna Prysiazhniuk,

Oleksandr Datsenko,

Олександр Поліщук

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(9)

Published: Jan. 22, 2024

The spiro[3.3]heptane core, with the non-coplanar exit vectors, was shown to be a saturated benzene bioisostere. This scaffold incorporated into anticancer drug sonidegib (instead of meta-benzene), vorinostat phenyl ring), and anesthetic benzocaine para-benzene). patent-free analogs obtained showed high potency in corresponding biological assays.

Language: Английский

Citations

6
Iron-Catalyzed Oxidative Rearrangement of Cyclopropanone Hemiaminals: General Access to Pyrroloindolones from Indoles DOI
Roger Machín Rivera,

Zack R. Ferrin,

Vincent N. G. Lindsay

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4738 - 4743

Published: May 29, 2024

A concise synthetic approach to medicinally relevant pyrroloindolones and related fused heterocycles is reported via the diastereoselective

Language: Английский

Citations

4
Heteroannulation of bicyclobutane derivativesviaAu-catalyzed hydration to enol ethers and intramolecular cyclization giving spirocyclobutanes DOI

Masaharu Takatsuki,

Hiroshi Aoyama, Kenichi Murai

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(48), P. 7467 - 7470

Published: Jan. 1, 2023

A heteroannulations of bicyclobutane derivatives is demonstrated to afford spirocyclobutanes with cyclic acetal groups via the Au-catalyzed hydration and subsequent intramolecular cyclization.

Language: Английский

Citations

9
1‐Oxa‐2,6‐diazaspiro[3.3]heptane as a New Potential Piperazine Bioisostere – Flow‐Assisted Preparation and Derivatisation by Strain‐Release of Azabicyclo[1.1.0]butanes DOI Creative Commons
Elena Graziano, Philipp Natho, Michael Andresini

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 23, 2024

Abstract The development of novel strained spiro heterocycles (SSHs) as bioisosteres for aromatic or non‐strained aliphatic rings is highly sought after improving drug design. Their high molecular rigidity and predictable vectorization can enhance drug‐likeness, target selectivity clinical success. Towards this goal, 1‐oxa‐2,6‐diazaspiro[3.3]heptane (ODASE) reported a potential SSH‐bioisostere. We demonstrate through theoretical studies the heterocycle to act bioisostere piperazine. have developed its synthesis from azabicyclo[1.1.0]butyl intermediate robust mild flow technology‐assisted two‐step protocol. Its tolerance stability towards medicinally relevant N ‐functionalisation protocols are studied, well reduction C3‐aminoalkylazetidinol motif found in anti‐cancer cobimetinib.

Language: Английский

Citations

3
Concise Synthesis of Optically Active Cyclopropane β-Amino Acid Derivatives via Olefination of Cyclopropanone Surrogates DOI
Myunggi Jung, Vincent N. G. Lindsay

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 10, 2025

An expedient synthesis of cyclopropane β-amino acid derivatives is reported from readily accessible cyclopropanone surrogates. The addition stabilized phosphorus ylides to 1-sulfonylcyclopropanols leads the formation highly electrophilic alkylidenecyclopropanes shown be reactive in a telescopic aza-Michael reaction, mild conditions. transformation proceeds with complete diastereocontrol favor trans products and amenable rapid production enantioenriched derivatives, peptidomimetics spirocyclic analogues.

Language: Английский

Citations

0
Formal Carbene Insertion into Cyclopropanones: Access to 2-Aroyl Cyclobutanones via Sulfonium Ylides DOI Creative Commons

Ishika Agrawal,

Meinolf Lange,

Arthur Semmelmaier

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 29, 2025

This report presents a method for the synthesis of 2-aroyl cyclobutanones via reaction in situ-generated cyclopropanones with acyl sulfonium ylides representing formal carbene insertion into cyclopropanones. The is highly stereoselective case 2-substituted cyclopropanones, and thus obtained are well suited to α-alkylation, offering versatile synthetic applications.

Language: Английский

Citations

0
Divergent Synthesis of β-Fluoroamides via Silver-Catalyzed Oxidative Deconstruction of Cyclopropanone Hemiaminals DOI
Yujin Jang,

Weixia Deng,

Ivan S. Sprague

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5389 - 5394

Published: July 6, 2023

An expedient approach for the synthesis of challenging β-fluoroamides from readily accessible cyclopropanone equivalents is reported. Following addition pyrazole used here as a transient leaving group, silver-catalyzed regiospecific ring-opening fluorination resulting hemiaminal leads to β-fluorinated

Language: Английский

Citations

7
Reductive Olefin Bicyclo[1.1.0]butane Coupling Enabled by Iron Hydride Hydrogen Atom Transfer DOI
Guang Chen,

Dayu Tian,

Xiaocheng Wang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 14928 - 14936

Published: Sept. 25, 2024

Language: Английский

Citations

2