Ring Expansion and 1,2‐Migration Cascade of Benzisoxazoles with Ynamides: Experimental and Theoretical Studies

Vanjari, Rajeshwer ; Dutta, Shubham ; Prabagar, B. ; Gandon, Vincent ; Sahoo, Akhila K. (2019) Ring Expansion and 1,2‐Migration Cascade of Benzisoxazoles with Ynamides: Experimental and Theoretical Studies Chemistry - An Asian Journal, 14 (24). pp. 4828-4836. ISSN 1861-4728

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Official URL: http://doi.org/10.1002/asia.201901251

Related URL: http://dx.doi.org/10.1002/asia.201901251

Abstract

Demonstrated herein is an AuI-catalyzed annulation of sulfonyl-protected ynamides with substituted 1,2-benzisoxazoles for the synthesis of E-benzo[e][1,3]oxazine derivatives. The transformation involves the addition of benzisoxazole to the gold-activated ynamide, ring expansion of the benzisoxazole fragment to provide an α-imino vinylic gold intermediate, and 1,2-migration of the sulfonamide motif to the masked carbene center to deliver the respective ring-expanded benzo[e][1,3]oxazine of predominant E configuration. A trapping experiment justifies the participation of the α-imino masked gold carbene. DFT computations also support the hypothesized mechanism and rationalize the product stereoselectivity.

Item Type:Article
Source:Copyright of this article belongs to John Wiley & Sons, Inc.
ID Code:121770
Deposited On:22 Jul 2021 07:08
Last Modified:22 Jul 2021 07:08

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