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Rhodium-catalyzed Sommelet–Hauser type rearrangement of α-diazoimines: synthesis of functionalized enamides
, Chandra Shekar Reddy Angula, Ramachandran Kuppan, Maheswar Reddy Palagulla
Published in Royal Society of Chemistry (RSC)
Volume: 56
Issue: 42
Pages: 5649 - 5652

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.

About the journal
JournalData powered by TypesetChemical Communications
PublisherData powered by TypesetRoyal Society of Chemistry (RSC)
Open AccessNo