Journal
CHEMICAL SCIENCE
Volume 6, Issue 10, Pages 5964-5968Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc01950h
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Funding
- National Science Council, Taiwan
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Gold-catalyzed hetero-[4 pi + 2 pi]-cycloadditions of tert-butyl propiolates with unactivated nitriles are described; the resulting 6H-1,3-oxazin-6-ones are not easily accessible via conventional methods. This new finding enables a one-pot gold-catalyzed synthesis of highly substituted pyridines through sequential gold-catalyzed reactions of tert-butyl propiolates with nitriles, and then with electrondeficient alkynes in the same solvent. The utility of these [4 + 2]-cycloadditions is further expanded with various aldehydes, ketones and 2-phenyloxetane, yielding satisfactory yields of cycloadducts.
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