Ring Expansion toward Fused Diazabicyclo[3.1.1]heptanes through Lewis Acid Catalyzed Highly Selective C−C/C−N Bond Cross‐Exchange Reaction between Bicyclobutanes and Diaziridines DOI
Heng-Xian He, Feng Wu, Xu Zhang

и другие.

Angewandte Chemie, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 13, 2024

Abstract The synthesis of bicyclic scaffolds has garnered considerable interest in drug discovery because their ability to mimic benzene bioisosteres. Herein, we introduce a new approach that utilizes Lewis acid (Sc(OTf) 3 )‐catalyzed σ‐bond cross‐exchange reaction between the C−C bond bicyclobutanes and C−N diaziridines produce multifunctionalized medicinally interesting azabicyclo[3.1.1]heptane derivatives. proceeds well with different broad range aryl‐ as alkenyl‐, but also alkyl‐substituted (up 98 % yield). Conducting scale‐up experiment exploring synthetic transformations cycloadducts emphasized practical application synthesis. Furthermore, zinc‐based chiral catalytic system was developed for enantioselective version this 96 ee ).

Язык: Английский

Palladium-Catalyzed Ligand-Controlled Switchable Hetero-(5 + 3)/Enantioselective [2σ+2σ] Cycloadditions of Bicyclobutanes with Vinyl Oxiranes DOI
Jin‐Lan Zhou, Yuanjiu Xiao,

Linke He

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(29), С. 19621 - 19628

Опубликована: Май 13, 2024

For nearly 60 years, significant research efforts have been focused on developing strategies for the cycloaddition of bicyclobutanes (BCBs). However, higher-order and catalytic asymmetric BCBs long-standing formidable challenges. Here, we report Pd-catalyzed ligand-controlled, tunable cycloadditions divergent synthesis bridged bicyclic frameworks. The dppb ligand facilitates formal (5+3) vinyl oxiranes, yielding valuable eight-membered ethers with scaffolds in 100% regioselectivity. Cy-DPEphos promotes selective hetero-[2σ+2σ] to access pharmacologically important 2-oxabicyclo[3.1.1]heptane (O-BCHeps). Furthermore, corresponding O-BCHeps 94–99% ee has achieved using chiral (S)-DTBM-Segphos, representing first cross-dimerization two strained rings. obtained are promising bioisosteres ortho-substituted benzenes.

Язык: Английский

Процитировано

48
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
Ring Expansion toward Fused Diazabicyclo[3.1.1]heptanes through Lewis Acid Catalyzed Highly Selective C−C/C−N Bond Cross‐Exchange Reaction between Bicyclobutanes and Diaziridines DOI
Heng-Xian He, Feng Wu, Xu Zhang

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 13, 2024

Abstract The synthesis of bicyclic scaffolds has garnered considerable interest in drug discovery because their ability to mimic benzene bioisosteres. Herein, we introduce a new approach that utilizes Lewis acid (Sc(OTf) 3 )‐catalyzed σ‐bond cross‐exchange reaction between the C−C bond bicyclobutanes and C−N diaziridines produce multifunctionalized medicinally interesting azabicyclo[3.1.1]heptane derivatives. proceeds well with different broad range aryl‐ as alkenyl‐, but also alkyl‐substituted (up 98 % yield). Conducting scale‐up experiment exploring synthetic transformations cycloadducts emphasized practical application synthesis. Furthermore, zinc‐based chiral catalytic system was developed for enantioselective version this 96 ee ).

Язык: Английский

Процитировано

11
Recent Progress in (3+3) Cycloadditions of Bicyclobutanes to Access Bicyclo[3.1.1]heptane Derivatives DOI
Jian‐Jun Feng

Synlett, Год журнала: 2024, Номер unknown

Опубликована: Авг. 28, 2024

Abstract The synthesis of bicyclo[3.1.1]heptane (BCHeps) derivatives, which serve as three-dimensional (3D) bioisosteres benzenes and are the core skeleton several terpene natural products, is garnering growing interest. (3+3) cycloadditions bicyclobutanes (BCBs) represent an attractive method for efficiently accessing (hetero)BCHep skeletons with 100% atom economy. Herein, we give a brief summary recent achievements in this approach diverse BCHep emphasizing our progress initial palladium-catalyzed vinyl oxiranes. 1 Introduction 2 Radical Cycloaddition Reaction 3 Polar 4 Palladium-Catalyzed Enantioselective 5 Conclusion

Язык: Английский

Процитировано

8
Enantioselective dearomative formal (3+3) cycloadditions of bicyclobutanes with aromatic azomethine imines: access to fused 2,3-diazabicyclo[3.1.1]heptanes DOI Creative Commons
Xue-Chun Yang, Feng Wu, Wen‐Biao Wu

и другие.

Chemical Science, Год журнала: 2024, Номер 15(46), С. 19488 - 19495

Опубликована: Янв. 1, 2024

We present the first enantioselective dearomative (3+3) cycloadditions of bicyclobutanes (BCBs) utilizing a chiral Lewis acid catalyst and bidentate chelating BCB substrates.

Язык: Английский

Процитировано

7
Recent Advances in the Synthesis of Bicyclo[3.1.1]heptanes DOI
Jianyang Dong, Dong Xue,

Huijuan Liao

и другие.

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Июль 16, 2024

Abstract In the past three years, bicyclo[3.1.1]heptanes and their structural analogues have emerged as useful bioisosteres of meta-substituted (hetero)arenes. To meet increasing demand for bicyclo[3.1.1]heptanes, chemists developed a plethora novel methods synthesis. this short review, we assess research progress on synthesis functionalization, considering both scope mechanistic aspects. addition, discuss posed challenges outlook identification new reaction manifolds to access functionalized bicyclo[3.1.1]heptanes. 1 Introduction 2 Synthesis Bicyclo[3.1.1]heptanes (BCHeps) 3 3-Azabicyclo[3.1.1]heptanes (3-Aza-BCHeps) 4 Conclusion Outlook

Язык: Английский

Процитировано

3
Advances in Photoinduced Minisci-like Reactions DOI

Mario Martos,

Irene Bosque, José C. González‐Gómez

и другие.

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Июль 29, 2024

Abstract The Minisci reaction, which has been around for more than five decades, is still the preferred tool straightforward alkylation of basic heteroarenes. recent developments in photocatalysis have opened novel pathways radical generation under milder and sustainable conditions. Implementing this approach into reaction renewed interest transformation, attractive per se Medicinal Chemistry. Aspects such as sacrificial oxidants, catalysts, specific conditions should be carefully examined to evaluate practicability protocol. This short review focuses on advances (2020 February 2024) photoinduced Minisci-type reactions, emphasizing sustainability. 1 Introduction 2 Using Noble-Metal-Based Photocatalysts 3 Noble-Metal-Free Methods Sacrificial Oxidants 4 Without 5 Conclusions Perspectives

Язык: Английский

Процитировано

3
Synthesis of bicyclo[3.1.1]heptanes, meta-substituted arene isosteres, from [3.1.1]propellane DOI
Bhaskar Paul, Ayan Dasgupta, Nils Frank

и другие.

Nature Protocols, Год журнала: 2025, Номер unknown

Опубликована: Фев. 17, 2025

Язык: Английский

Процитировано

0
Computational Access to 1,3,5,6,7‐Pentanitro‐3,6,7‐Triazabicyclo‐[3.1.1]‐Heptane (UIX): A Powerful Potential Explosive with Zero Oxygen Balance DOI
Sohan Lal, Haixiang Gao, Jean’ne M. Shreeve

и другие.

Chemistry - An Asian Journal, Год журнала: 2025, Номер unknown

Опубликована: Май 14, 2025

Abstract A novel cage nitramine, and potential explosive, 1,3,5,6,7‐pentanitro‐3,6,7‐triazabicyclo‐[3.1.1]‐heptane (UIX) with a zero‐oxygen balance was designed. It has high crystal density (ρ = 1.978 g/cm 3 ), outstanding propulsive detonation properties (Isp(s) neat 269.61; ρIsp(g cm −3 s) 533.29; P 42.55 GPa, D 9620 m/s), good sensitivity (h 50 9.06 cm) promising kinetic stability as CL‐20. Additionally, synthesis route for UIX is proposed.

Язык: Английский

Процитировано

0
Ring Expansion toward Fused Diazabicyclo[3.1.1]heptanes through Lewis Acid Catalyzed Highly Selective C−C/C−N Bond Cross‐Exchange Reaction between Bicyclobutanes and Diaziridines DOI
Heng-Xian He, Feng Wu, Xu Zhang

и другие.

Angewandte Chemie, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 13, 2024

Abstract The synthesis of bicyclic scaffolds has garnered considerable interest in drug discovery because their ability to mimic benzene bioisosteres. Herein, we introduce a new approach that utilizes Lewis acid (Sc(OTf) 3 )‐catalyzed σ‐bond cross‐exchange reaction between the C−C bond bicyclobutanes and C−N diaziridines produce multifunctionalized medicinally interesting azabicyclo[3.1.1]heptane derivatives. proceeds well with different broad range aryl‐ as alkenyl‐, but also alkyl‐substituted (up 98 % yield). Conducting scale‐up experiment exploring synthetic transformations cycloadducts emphasized practical application synthesis. Furthermore, zinc‐based chiral catalytic system was developed for enantioselective version this 96 ee ).

Язык: Английский

Процитировано

0