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Synthesis 2025; 57(01): 167-175
DOI: 10.1055/s-0043-1775381
DOI: 10.1055/s-0043-1775381
paper
Special Topic Dedicated to Prof. H. Ila
Zinc Carbenoid-Promoted Methylene Insertion in Saturated Heterocycles: Mechanistic Insights and Reactivity Profiles
Authors
This work was supported by JSPS Fellowship (23KJ0899) from the Japan Society for the Promotion of Science.
Dedicated to Professor Hiriyakkanavar Ila on her 80th birthday
Abstract
The ring expansion of saturated heterocycles through methylene insertion into N–O bonds using a zinc carbenoid is described. This transformation is applied to 1,2-oxazetidines and 1,2-oxazolidines, while N-tosylated 1,2-oxazinane affords a ring-opened product. Density functional theory calculations suggest a stepwise reaction mechanism of the ring expansion and elucidate the origins of the different reactivities observed.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775381.
- Supporting Information (PDF)
Publication History
Received: 19 May 2024
Accepted after revision: 19 June 2024
Article published online:
16 July 2024
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