Partial reduction of pyridinium salts as a versatile route to dihydropyridones

Organic Letters

Volumn 7, Issue 3, 2005, Pages 435-437

  Donohoe, Timothy J ^a   Johnson, Dale J ^a   Mace, Laura H ^a   Bamford, Mark J ^b   Ichihara, Osamu ^c  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c EVOTEC UK LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKYL GROUP; CARBONYL DERIVATIVE; HALIDE; HYDROGEN; PYRIDINIUM DERIVATIVE; PYRIDONE DERIVATIVE;

ADDITION REACTION; ARTICLE; ELECTRON TRANSPORT; HYDROLYSIS; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; REACTION ANALYSIS; REDUCTION KINETICS; STANDARD; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

CRYSTALLOGRAPHY, X-RAY; ELECTRONS; HYDROLYSIS; INDICATORS AND REAGENTS; PYRIDINIUM COMPOUNDS; PYRIDONES;

EID: 13844299285     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0476624     Document Type: Article

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27. The NOE experiments were performed on the major diastereoisomer of 19. Irradiation of the C-7 methyl group showed a strong enhancement to the proton attached to C-6 but no enhancement of the methyl group attached to C-2. However, irradiation of the C-2 methyl group showed a strong enhancement to the proton on C-6. Finally, irradiation of the C-6 proton showed strong enhancement to both methyl groups at C-2 and C-7.