Gaykar, Rahul N. ; George, Malini ; Guin, Avishek ; Bhattacharjee, Subrata ; Biju, Akkattu T. (2021) An Umpolung Oxa-[2,3] Sigmatropic Rearrangement Employing Arynes for the Synthesis of Functionalized Enol Ethers Organic Letters, 23 (9). pp. 3447-3452. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/acs.orglett.1c00911
Related URL: http://dx.doi.org/10.1021/acs.orglett.1c00911
Abstract
An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C═O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic studies rule out the possibility of Pummerer-type rearrangement operating in this case.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society |
| ID Code: | 128586 |
| Deposited On: | 03 Nov 2022 06:37 |
| Last Modified: | 11 Nov 2022 06:43 |
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