Stereoselective Vinylogous Aza-Pummerer Reaction of β,β-Disubstituted Enesulfinamides

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

Published: Jan. 9, 2025

Treatment of multisubstituted NH-enesulfinamides with tosyl isocyanate (TsNCO) at room temperature results in the formation α-tosylcarbamoyloxy N-sulfenyl ketimines high enantioselectivity. This process is believed to proceed via a vinylogous aza-Pummerer-type reaction pathway which sulfinyl oxygen atom enesulfinamides undergoes nucleophilic attack on isocyanate, triggering subsequent transformations that enable transfer chirality from sulfur carbon.

Language: Английский

Stereoselective Enesulfinamide–Sulfinylimine Tautomerization of β,β-Disubstituted Enesulfinamides

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

In the presence of cesium fluoride and organosilicon reagent, β,β-disubstituted NH-enesulfinamides undergo stereoselective enesulfinamide-sulfinylimine tautomerization at room temperature, resulting in formation α-branched

Language: Английский