Sarkar, D and Deswal, S and Chandra Das, R and Biju, AT (2024) Lewis acid-catalyzed (3 + 2) annulation of bicyclobutanes with ynamides: access to 2-amino-bicyclo2.1.1hexenes. In: Chemical Science .
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Abstract
Strain-release driven annulations with bicyclo1.1.0butanes (BCBs) have become an attractive area of research for the synthesis of bioisosteric bicyclohexane derivatives, which play a vital role in drug discovery. Interestingly, the utilization of the inherent strain in BCBs for the synthesis of functionalized amino-bicyclo2.1.1hexenes, which may spatially mimic substituted benzenes and anilines, has received only scant attention. Herein, we report the Sc(OTf)3-catalyzed (3 + 2) annulation of BCBs with ynamides for the facile synthesis of 2-amino-bicyclo2.1.1hexenes in one step under mild conditions. The reaction likely proceeds via nucleophilic addition facilitated by the nitrogen lone pair from the alkynyl group of the ynamides to the unsubstituted side of the BCBs, followed by the annulation of the resulting enolate with the keteniminium species. For the first time, the C-C triple bond of ynamides was utilized as the coupling partner for BCBs, resulting in products adorned with a functionalizable amino group and an integrated strained alkene moiety. © 2024 The Royal Society of Chemistry.
| Item Type: | Journal Article |
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| Publication: | Chemical Science |
| Publisher: | Royal Society of Chemistry |
| Additional Information: | The copyright for this article belongs to the authors. |
| Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
| Date Deposited: | 18 Oct 2024 04:45 |
| Last Modified: | 18 Oct 2024 04:45 |
| URI: | http://eprints.iisc.ac.in/id/eprint/86367 |
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