Gold-Catalyzed Stereoselective Synthesis of Polysubstituted Indanes

Gold-Catalyzed Formal (3+2) Cycloaddition in an Ionic Liquid: Environmentally Friendly and Stereoselective Synthesis of Polysubstituted Indanes from Benzylic Alcohols and 1-Phenylpropenes: N. Morita, H. Chiaki, K. Ikeda, K. Tanaka III, Y. Hashimoto, O. Tamura
Synlett 2023, DOI: 10.1055/a-2002-4122


Polysubstituted indanes are of great interest, mainly because of their diverse – and occasionally potent – biological properties, which include anti-inflammatory, fungicide, insecticide, and sedative activities. Existing synthetic methods are seldom catalytic and often require the use of toxic volatile halogenated solvents, such as CH2Cl2 or CHCl3. Recently, the group of Dr. Nobuyoshi Morita and Professor Osamu Tamura from Showa Pharmaceutical University (Machida, Tokyo, Japan) reported a novel approach to the target compounds.

Dr. Morita said: “We have developed an environmentally friendly and stereoselective method for the synthesis of polysubstituted indanes via gold-catalyzed formal (3+2) cycloaddition of benzylic alcohols and 1-phenylpropene in ionic liquids. This reaction is both environmentally and economically advantageous because it does not require the use of toxic volatile halogenated solvents or stoichiometric amounts of reagents, and the gold catalyst and ionic liquid can be recycled multiple times.”

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