Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 22, Pages 8470-8473Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja202576e
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- MEXT
- Grants-in-Aid for Scientific Research [22790009, 22106522] Funding Source: KAKEN
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The torquoselectivity of the 4 pi electrocyclic ring-opening reaction of 2-azetines can be controlled by the Bronsted acidity of the catalyst and the polarity of the solvent. DFT calculations provided insight into the mechanism of this remarkable switch. Anti and syn stereoisomers of alpha,beta-unsaturated amidines were selectively synthesized from ynamides and aldimines in the presence of Tf(2)NH and CSA, respectively.
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