Structurally divergent reactivity of 2,2-disubstituted azetidines – mechanistic insights and stereochemical implications of amide coupling and ring expansion to 5,6-dihydro-4 <i>H</i> -1,3-oxazines
Subjecting 2,2-disubstituted azetidines to amide coupling with carboxylic acids is found to effect either N -acylation or ring expansion to spiro- and 6,6-disubstituted 5,6-dihydro-4 H -1,3-oxazines, dependent on the reaction conditions.
Authors
- Alan C. Spivey (ORCID: https://orcid.org/0000-0001-5114-490X)
- James A Bull
- Xiurong Zhang (ORCID: https://orcid.org/0000-0002-7384-9748)
- Callum S Begg
- Aditya K. Sahay
Institutions
- Signature Research (United States) (US)
- Imperial College London (GB)
Publication Details
- Journal
- Organic Chemistry Frontiers
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5qo00804b
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Royal Society
- Engineering and Physical Sciences Research Council