Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles

3-Azabicyclo[3.1.0]hexanes are common structural components in natural products and bioactive compounds. Traditionally, the metal-mediated cyclopropanation domino reaction of chain enzymes is the most commonly used strategy for the construction of this type of aza[3.1.0]bicycle derivative. In this s...

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Published inMolecules (Basel, Switzerland) Vol. 28; no. 9; p. 3691
Main Authors Li, Jingya, Zhang, Zhiguo, Chen, Liming, Li, Mengjuan, Zhang, Xingjie, Zhang, Guisheng
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 25.04.2023
MDPI
Subjects
addition of alkenes
Alkenes
amination
aza[3.1.0]bicycles
Bicycles
Bioactive compounds
Biological activity
Cascade chemical reactions
Chromatography
Cyclopropane compounds
Hexanes
Natural products
NMR
Nuclear magnetic resonance
Solvents
vinyl cyclopropanecarboxamides
amination
addition of alkenes
vinyl cyclopropanecarboxamides
aza[3.1.0]bicycles
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Summary:3-Azabicyclo[3.1.0]hexanes are common structural components in natural products and bioactive compounds. Traditionally, the metal-mediated cyclopropanation domino reaction of chain enzymes is the most commonly used strategy for the construction of this type of aza[3.1.0]bicycle derivative. In this study, a base-promoted intramolecular addition of alkenes used to deliver conformationally restricted highly substituted aza[3.1.0]bicycles is reported. This reaction was tailor-made for saturated aza[3.1.0] bicycle-containing fused bicyclic compounds that may be applied in the development of concise and divergent total syntheses of bioactive compounds.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28093691