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Scandium‐Catalyzed Cascade Cyclization to Produce Cyclobutane‐Fused Tetrahydroquinoline, Chromane, Thiochromane, and Tetrahydronaphthalene Derivatives
Author(s) -
Nakano Shunichi,
Kakugawa Kazumi,
Nemoto Tetsuhiro,
Hamada Yasumasa
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400020
Subject(s) - cyclobutane , chemistry , scandium , trifluoromethanesulfonate , catalysis , aldol reaction , cascade , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , ring (chemistry) , chromatography
We have succeeded in the highly diastereoselective synthesis of cyclobutane‐fused multi‐cyclic 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.