Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
Rigid bicycles are becoming more popular in the pharmaceutical industry because they allow for expansion to new and unique chemical spaces. This work describes a new strategy to construct 2-azanorbornanes, which can act as rigid piperidine/pyrrolidine scaffolds with well-defined exit vectors. To achieve the synthesis of 2-azanorbornanes, new strain-release reagent, azahousane, is introduced along with its photosensitized strain-release formal cycloaddition with alkenes. Furthermore, new reactivity between a housane and an imine is disclosed. Both strategies lead to various substituted 2-azanorbornanes with good selectivities.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10760907 | PMC |
| http://dx.doi.org/10.1002/anie.202314700 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Enantioselective Synthesis of 2-Azanorbornanes: Chiral Trisimidazoline-Catalyzed Desymmetrizing Transannular Bromoaminocyclization.
Org Lett
April 2025
Anhui Province Key Laboratory of Value-Added Catalytic Conversion and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China.
An enantioselective desymmetrizing transannular bromoaminocyclization of cyclopentenylamines has been achieved by using -symmetric trisimidazoline catalysis. This protocol could directly provide a range of chiral 2-azanorbornanes in excellent yields (up to 99%) and enantioselectivities (up to 97.5:2.
View Article and Find Full Text PDFSynthesis of 2-Azanorbornanes via Strain-Release Formal Cycloadditions Initiated by Energy Transfer.
Angew Chem Int Ed Engl
December 2023
Department of Chemistry, Indiana University, 800 E. Kirkwood Ave. Bloomington, IN, 47401, USA.
Article Synopsis
- Rigid bicycles are increasingly favored in the pharmaceutical sector for exploring new chemical possibilities.
- A novel method for creating 2-azanorbornanes is presented, which serve as rigid scaffolds with specific exit vectors.
- The development involves a strain-release reagent called azahousane and a new reaction with alkenes and imines, yielding various substituted 2-azanorbornanes with high selectivity.
Approaches to syn-7-substituted 2-azanorbornanes as potential nicotinic agonists; synthesis of syn- and anti-isoepibatidine.
Org Lett
June 2005
Department of Chemistry, University of Leicester, Leicester LE1 7RH, United Kingdom.
[reaction: see text] Coupling of N-Boc-7-bromo-2-azabicyclo[2.2.1]heptane with aryl and pyridyl boronic acids incorporates aryl and heterocyclic substituents at the 7-position and leads to a preference for syn over anti stereoisomers.
View Article and Find Full Text PDF