Umpolung Reactivity of Ynamides: An Unconventional [1,3]‐Sulfonyl and [1,5]‐Sulfinyl Migration Cascade

Prabagar, B. ; Mallick, Rajendra K. ; Prasad, Rangu ; Gandon, Vincent ; Sahoo, Akhila K. (2019) Umpolung Reactivity of Ynamides: An Unconventional [1,3]‐Sulfonyl and [1,5]‐Sulfinyl Migration Cascade Angewandte Chemie International Edition, 58 (8). pp. 2365-2370. ISSN 1433-7851

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Official URL: http://doi.org/10.1002/anie.201813143

Related URL: http://dx.doi.org/10.1002/anie.201813143

Abstract

A regioselective sulfonyl/sulfinyl migration cycloisomerization cascade of alkyne-tethered ynamides is developed in the presence of XPhosgold catalyst. This reaction is the first example of a general [1,3]-sulfonyl migration from the nitrogen center to the β-carbon atom of ynamides, followed by umpolung 5-endo-dig cyclization of the ynamide α-carbon atom to the gold-activated alkyne, and final deaurative [1,5]-sulfinylation. This process allows the synthesis of peripherally decorated unconventional 4-sulfinylated pyrroles with broad scope from N-propargyl-tethered ynamides. In contrast, N-homopropargyl-tethered ynamides undergo intramolecular tetradehydro Diels–Alder reaction to provide 2,3-dihydro-benzo[f]indole derivatives. Control experiments and density-functional theory studies were used to study the reaction pathways.

Item Type:Article
Source:Copyright of this article belongs to John Wiley & Sons, Inc.
ID Code:121780
Deposited On:22 Jul 2021 07:37
Last Modified:22 Jul 2021 07:37

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