An Umpolung Oxa-2,3 Sigmatropic Rearrangement Employing Arynes for the Synthesis of Functionalized Enol Ethers

Gaykar, RN and George, M and Guin, A and Bhattacharjee, S and Biju, AT (2021) An Umpolung Oxa-2,3 Sigmatropic Rearrangement Employing Arynes for the Synthesis of Functionalized Enol Ethers. In: Organic Letters, 23 (9). pp. 3447-3452.

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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. © 2021 American Chemical Society.

Item Type:	Journal Article
Publication:	Organic Letters
Publisher:	American Chemical Society
Additional Information:	The copyright for this article belongs to American Chemical Society
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	22 Jul 2021 06:25
Last Modified:	22 Jul 2021 06:25
URI:	http://eprints.iisc.ac.in/id/eprint/68884

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