Aza-Darzens Type Reaction of Azirines: Access to Highly Substituted 1-Azabicyclo[1.1.0]butanes and Azetidines
Abstract
A streamlined approach was developed for accessing 2,3,4-substituted 1-azabicyclo[1.1.0]butanes from azirines under aza-Darzens-type reaction conditions. The pronounced ring strain in these bicyclic systems enabled distinctive electrophilic transformations via activation of the N-C(3) bond, leading to the formation of substituted azetidines. The relative configurations of the 1-azabicyclo[1.1.0]butanes were established by 2D NMR, while single-crystal X-ray analysis of the azetidines confirmed their structures and, by analogy, supported the configurational assignments of both these synthesized classes.
Fields of Study & Subjects
Synthesis and Catalytic Reactions
Asymmetric Synthesis and Catalysis
Radical Photochemical Reactions
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 4
- Pages
- 1724–1730
- Publication date
- 15 January 2026
- Language
- EN