Highly diastereoselective synthesis of tetralin-fused spirooxindoles via lewis acid-catalyzed C(sp3)H bond functionalization
A highly diastereoselective synthesis of tetralin-fused spirooxindole derivatives was described. Treatment of benzylidene oxindoles with a catalytic amount of Sc(OTf)3 in refluxing hexane afforded the target compounds in good chemical yields with excellent diastereoselectivities (up to >20:1). Detailed investigation of the reaction mechanism revealed that both interconversion of the two diastereomers and their solubility difference in reaction medium were the key to achieving excellent diastereoselectivities.
Machida, Mizuki,Mori, Keiji
p. 868 - 871
(2018/07/03)
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