Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 42, Pages 8914-8922Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob01699a
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Funding
- European Research Council under the European Union [279850]
- EPSRC [EP/J018139/1]
- Royal Society
- EPSRC [EP/J018139/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/J018139/1] Funding Source: researchfish
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The scope and limitations of a photoinitiated N- to C-sulfonyl migration process within a range of dihydropyridinones is assessed. This sulfonyl transfer proceeds without erosion of either diastereo- or enantiocontrol, and is general across a range of N-sulfonyl substituents (SO2R; R = Ph, 4-MeC6H4, 4-MeOC6H4, 4-NO2C6H4, Me, Et) as well as C(3)-(aryl, heteroaryl, alkyl and alkenyl) and C(4)-(aryl and ester) substitution. Crossover reactions indicate an intermolecular step is operative within the formal migration process, although no crossover from C-sulfonyl products was observed. EPR studies indicate the intermediacy of a sulfonyl radical and a mechanism is proposed based upon these observations.
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