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Unified Synthesis of Cycloheptatriene-Fused Heterobicyclo[3.1.1]heptanes by Lewis Acid-Catalyzed Higher-Order (8 + 3) Cycloaddition of Bicyclo[1.1.0]butanes with Troponoids.

Organic Letters
Herein, we developed a unified strategy to synthesize three libraries of medicinally attractive cycloheptatriene-fused heterobicyclo[3.1.1]heptanes (X-BCHeps, X = N, O, S) through a Lewis acid-catalyzed higher-order (8 + 3) cycloaddition of bicyclo[1.1.0]
Chao Peng   +7 more
semanticscholar   +1 more source

3-Oxabicyclo[3.1.1]heptanes as Isosteres of meta-Substituted Benzene Rings.

Organic Letters
Replacement of the aromatic rings in drug candidates with isosteric rigid sp3-rich scaffolds can improve physicochemical properties, increase the chance of progressing the molecule in development, and open new chemical space.
Jennifer Morvan   +3 more
semanticscholar   +1 more source

Strain-Enabled Radical-Polar Crossover Annulation to Access Spiro-, Fused-, and Enantioenriched-Aza/Oxa-Bicyclo[3.1.1]heptanes.

Angewandte Chemie
Conformationally rigid bridged bicyclic scaffolds have emerged as bioisosteric replacements for planar aromatic rings. However, bioisosteric mimetics of heteroaromatic rings have been investigated less due to the challenges of incorporating heteroatoms ...
Bhismalochan Ghorai   +2 more
semanticscholar   +1 more source

Synthesis of Bicyclo[2.2.1]Heptanes via Pyridine-Boronyl Radical-Catalyzed [2π + 2σ] Cycloaddition.

Journal of Organic Chemistry
Bicyclo[2.2.1]heptanes (BCHeps) are essential polycyclic compounds in many natural products and pharmaceutical molecules. Efficient synthetic strategies for BCHeps and their derivatives are desirable and challenging. In this work, bicyclo[2.1.0]pentanes (
Saima Perveen   +7 more
semanticscholar   +1 more source

Chalcogen Bonding Activates [1.1.1]Propellane: Constructing Spiro[3.3]heptanes via Cyclobutyl Insertion into Cyclopropenones.

Journal of the American Chemical Society
Chalcogen bonding catalysis has recently emerged as a new platform in organic synthesis, enabling the achievement of a diverse array of reactions. All of these chalcogen bonding catalyzed reactions rely on the interactions with lone-pair and π electrons.
Ziqiang Zhao, Yao Wang
semanticscholar   +1 more source

Photoexcited Copper-Catalyzed Intramolecular [2+2] Cycloaddition To Construct Bicyclo[3.2.0]heptanes.

Organic Letters
The bicyclo[3.2.0]heptane scaffold is frequently found in a wide range of bioactive molecules and plays a pivotal role in constructing key modules of these compounds.
Hongling Xie, Shouyun Yu
semanticscholar   +1 more source

Synthesis of Indole-Fused Bicyclo[3.1.1]heptanes through (3+3) Cycloaddition of 2-Indolylmethanols with Bicyclo[1.1.0]butanes.

Organic Letters
A variety of indole-fused bicyclo[3.1.1]heptanes were prepared in good yields with high regioselectivity through organocatalyzed umpolung (3+3) cycloaddition of 2-indolylmethanols and bicyclo[1.1.0]butanes (BCBs) under mild reaction conditions.
Cheng-Jing Li   +5 more
semanticscholar   +1 more source

Fluorine‐containing 6‐Azabicyclo[3.1.1]heptanes: Bicyclic Piperidine Analogs for Drug Discovery

Annalen der Pharmacie
Convenient synthetic approaches to a series of fluorinated bicyclic piperidine analogs (including 3‐fluoro‐, 3,3‐difluoro‐, 3‐carboxy‐3‐fluoro‐, and 3‐trifluoromethyl‐substituted 6‐azabicyclo­[3.1.1]heptanes) were proposed.
Anton V. Chernykh   +8 more
semanticscholar   +1 more source

Lewis-Acid-Catalyzed Dearomative [4π + 2σ] Cycloaddition of Bicyclobutanes with Isoquinolinium Methylides for the Synthesis of Ring-Fused Azabicyclo[3.1.1]heptanes.

Organic Letters
Dearomative cycloadditions are valuable for efficiently generating three-dimensional molecular complexity. However, despite recent reports of cycloadditions of bicyclobutanes (BCBs) for the synthesis of aza-bicyclo[3.1.1]heptanes (aza-BCHeps), which are ...
Qin Jiang   +5 more
semanticscholar   +1 more source

Recent Advances in the Synthesis of Bicyclo[3.1.1]heptanes

Synthesis
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 the increasing demand for bicyclo[3.1.1]heptanes, chemists have developed a plethora of novel ...
Jianyang Dong, Huijuan Liao, Dong Xue
semanticscholar   +1 more source

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