Journal
ORGANIC LETTERS
Volume 5, Issue 21, Pages 3899-3902Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0355130
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- NIGMS NIH HHS [GM-49093] Funding Source: Medline
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[GRAPHICS] Alkyl azides react with saturated ketones upon treatment with Lewis acids to afford ring-expansion products through the azido-Schmidt reaction, but this reaction does not proceed when alpha,beta-unsaturated ketones are used. In this study, alkyl azides were reacted with enones in the presence of Lewis acids to give enaminones (vinylogous amides), which formally involve a ring contraction reaction. The mechanism and scope of this reaction is discussed.
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