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

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N- to C-sulfonyl photoisomerisation of dihydropyridinones : a synthetic and mechanistic study. / Yeh, Pei-Pei; Taylor, James Edward; Stark, Daniel Graham; Daniels, David Sydney Bernard; Fallan, Charlene; Walton, John Christopher; Smith, Andrew David.

In: Organic & Biomolecular Chemistry, Vol. In press, 16.10.2017.

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Yeh, P-P, Taylor, JE, Stark, DG, Daniels, DSB, Fallan, C, Walton, JC & Smith, AD 2017, 'N- to C-sulfonyl photoisomerisation of dihydropyridinones: a synthetic and mechanistic study' Organic & Biomolecular Chemistry, vol In press. DOI: 10.1039/C7OB01699A

APA

Yeh, P-P., Taylor, J. E., Stark, D. G., Daniels, D. S. B., Fallan, C., Walton, J. C., & Smith, A. D. (2017). N- to C-sulfonyl photoisomerisation of dihydropyridinones: a synthetic and mechanistic study. Organic & Biomolecular Chemistry, In press. DOI: 10.1039/C7OB01699A

Vancouver

Yeh P-P, Taylor JE, Stark DG, Daniels DSB, Fallan C, Walton JC et al. N- to C-sulfonyl photoisomerisation of dihydropyridinones: a synthetic and mechanistic study. Organic & Biomolecular Chemistry. 2017 Oct 16;In press. Available from, DOI: 10.1039/C7OB01699A

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Yeh, Pei-Pei; Taylor, James Edward; Stark, Daniel Graham; Daniels, David Sydney Bernard; Fallan, Charlene; Walton, John Christopher; Smith, Andrew David / N- to C-sulfonyl photoisomerisation of dihydropyridinones : a synthetic and mechanistic study.

In: Organic & Biomolecular Chemistry, Vol. In press, 16.10.2017.

Research output: Contribution to journalArticle

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@article{daca5ef17726428a864d578d85a47c6f,
title = "N- to C-sulfonyl photoisomerisation of dihydropyridinones: a synthetic and mechanistic study",
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.",
author = "Pei-Pei Yeh and Taylor, {James Edward} and Stark, {Daniel Graham} and Daniels, {David Sydney Bernard} and Charlene Fallan and Walton, {John Christopher} and Smith, {Andrew David}",
note = "The authors thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC Grant Agreement no. 279850 (CF and JET) and EPSRC grant number EP/J018139/1 (DSBD) for funding. ADS thanks the Royal Society for a Wolfson Research Merit Award.",
year = "2017",
month = "10",
doi = "10.1039/C7OB01699A",
volume = "In press",
journal = "Organic & Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - N- to C-sulfonyl photoisomerisation of dihydropyridinones

T2 - Organic & Biomolecular Chemistry

AU - Yeh,Pei-Pei

AU - Taylor,James Edward

AU - Stark,Daniel Graham

AU - Daniels,David Sydney Bernard

AU - Fallan,Charlene

AU - Walton,John Christopher

AU - Smith,Andrew David

N1 - The authors thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC Grant Agreement no. 279850 (CF and JET) and EPSRC grant number EP/J018139/1 (DSBD) for funding. ADS thanks the Royal Society for a Wolfson Research Merit Award.

PY - 2017/10/16

Y1 - 2017/10/16

N2 - 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.

AB - 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.

UR - http://www.rsc.org/suppdata/c7/ob/c7ob01699a/c7ob01699a1.pdf

U2 - 10.1039/C7OB01699A

DO - 10.1039/C7OB01699A

M3 - Article

VL - In press

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

ER -

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