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Issue 42, 2017
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N- to C-sulfonyl photoisomerisation of dihydropyridinones: a synthetic and mechanistic study

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Abstract

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.

Graphical abstract: N- to C-sulfonyl photoisomerisation of dihydropyridinones: a synthetic and mechanistic study

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Publication details

The article was received on 11 Jul 2017, accepted on 08 Aug 2017 and first published on 16 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB01699A
Citation: Org. Biomol. Chem., 2017,15, 8914-8922
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    N- to C-sulfonyl photoisomerisation of dihydropyridinones: a synthetic and mechanistic study

    P. Yeh, J. E. Taylor, D. G. Stark, D. S. B. Daniels, C. Fallan, J. C. Walton and A. D. Smith, Org. Biomol. Chem., 2017, 15, 8914
    DOI: 10.1039/C7OB01699A

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