Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 40, Pages 13219-13221Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja804078v
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Funding
- Deutsche Forschungsgemeinschaft [JA1072/4-1, AR493/1-1, -2]
- Fonds der Chemischen Industrie
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An efficient cycloaddition reaction of 1-alkoxy-1-azadienes with alpha,alpha-dicyanoalkenes is described, which gives facile access to highly substituted 3-hydroxypyridines in very good yields and with complete regiocontrol and chemoselectivity. The reaction path was investigated in detail by quantum mechanics calculations, reporting that a concerted cycloaddition mechanism and thermodynamic control synergistically contribute to the observed selectively.
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