Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 14, Pages 7628-7636Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00838
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Funding
- Japan Society for the Promotion of Science (JSPS) [15H03802]
- MEXT (Japan) program Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions of Hokkaido University
- Grants-in-Aid for Scientific Research [15H03802] Funding Source: KAKEN
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Aza-Diels Alder-type cycloaddition reactions between a range of N-arylimines and functionalized alkenes were effectively catalyzed by the Cr(III)/bipyridine complex under irradiation of blue light, to give the corresponding 1,2,3,4tetrahydroquinoline derivatives in high yields with excellent diastereoselectivity. Typically, the reaction of benzylideneaniline with 1-vinyl-2-pyrrolidinone proceeded smoothly with a substrate-to catalyst molar ratio (S/C) of 1000 and completed within 4 h at room temperature (20-25 degrees C), affording the cycloaddition product in 97% yield.
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