Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 9, Pages 2088-2096Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201400020
Keywords
cascade catalysis; cyclization; cyclobutanes; scandium; tetrahydroquinolines
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Funding
- Ministry of Educationx, Culture, Sports, Science, and Technology, Japan
- Chiba University
- Uehara Memorial Foundation
- Grants-in-Aid for Scientific Research [23390003] Funding Source: KAKEN
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We have succeeded in the highly diastereoselective synthesis of cyclobutane-fused multicyclic compounds using a scandium-catalyzed cascade cyclization. Using 3-10 mol% of scandium(III) triflate [Sc(OTf)(3)], various cyclobutane-fused tetrahydroquinoline derivatives as well as its chromane, thiochromane, and tetrahydronaphthalene analogues were obtained in good to excellent yields. Derivatizations of the reaction products, as well as the plausible reaction mechanism, are also discussed.
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