[2,3] Sigmatropic Rearrangement of Allylic S-Acylsulfonium Ylide Intermediates Generated from Rhodium-Catalyzed Addition of Diazo Compounds DOI

C. M. CRIBBS,

Jason R. Combs,

Viktor Gevirtzman

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 7, 2025

Allyl thioesters, thiocarbonates, thiocarbamates, and thiocyanates are shown to undergo rhodium-catalyzed addition of carbene groups, generated from diazo compounds, afford S-acyl sulfonium ylides that [2,3] sigmatropic rearrangement. Competing side reactions such as cyclopropanation [1,2] acyl shifts not observed. The reaction works with a variety sulfur functional including thiocyanates, affording densely functionalized products. well trimethylsilyldiazomethane (TMSD) α-aryl diazoesters.

Language: Английский

[2,3] Sigmatropic Rearrangement of Allylic S-Acylsulfonium Ylide Intermediates Generated from Rhodium-Catalyzed Addition of Diazo Compounds DOI

C. M. CRIBBS,

Jason R. Combs,

Viktor Gevirtzman

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 7, 2025

Allyl thioesters, thiocarbonates, thiocarbamates, and thiocyanates are shown to undergo rhodium-catalyzed addition of carbene groups, generated from diazo compounds, afford S-acyl sulfonium ylides that [2,3] sigmatropic rearrangement. Competing side reactions such as cyclopropanation [1,2] acyl shifts not observed. The reaction works with a variety sulfur functional including thiocyanates, affording densely functionalized products. well trimethylsilyldiazomethane (TMSD) α-aryl diazoesters.

Language: Английский

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