Rhodium-catalyzed Sommelet–Hauser type rearrangement of α-diazoimines: synthesis of functionalized enamides. Issue 42 (21st April 2020)

• Record Type: Journal Article
• Authors: Reddy, Angula Chandra Shekar; Ramachandran, Kuppan; Reddy, Palagulla Maheswar; Anbarasan, Pazhamalai
• Is Part Of: Chemical communications. Volume 56:Issue 42(2020)
• Page Start: 5649
• Page End: 5652
• Publication Date: 2020-04-21
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d0cc00016g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : An efficient rhodium catalyzed Sommelet–Hauser type rearrangement of sulfur ylides derived from α-thioesters and N -sulfonyl-1, 2, 3-triazoles has been successfully accomplished for the synthesis of various functionalized enamides. Abstract : An efficient rhodium catalyzed Sommelet–Hauser type rearrangement of sulfur ylides derived from α-thioesters and N -sulfonyl-1, 2, 3-triazoles has been successfully accomplished for the synthesis of various functionalized enamides. The developed reaction involves the unprecedented [2, 3]-sigmatropic rearrangement of sulfur ylides with the imine motif. Importantly, the method works well with various substituted α-thioesters/-amides/-ketones and substituted N -sulfonyl-1, 2, 3-triazoles and allows the synthesis of diverse enamide derivatives in good to excellent yields. The reaction was also successfully extended to the one-pot synthesis of enamides from terminal alkynes.