Volume 20, Issue 18
Preparative Organic Chemistry
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ChemInform Abstract: Applications of Phase-Transfer Catalysis. Part 45. Enantioselective Phase-Transfer Catalysis by Optically Active Crown Ethers.

E. V. DEHMLOW

E. V. DEHMLOW

Fak. Chem., Univ. Bielefeld, D-4800 Bielefeld 1

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C. SAUERBIER

C. SAUERBIER

Fak. Chem., Univ. Bielefeld, D-4800 Bielefeld 1

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First published: May 2, 1989

Abstract

A series of 11 optically active crown ethers are probed as enantioselective phase-transfer catalysts in the epoxidation of unsaturated ketones by hypochlorite and in the addition of cyanide to these compounds.

ChemInform Abstract

A series of 11 optically active crown ethers are probed as enantioselective phase-transfer catalysts in the epoxidation of unsaturated ketones by hypochlorite and in the addition of cyanide to these compounds. Best results with up to 45% e.e. are obtained in the synthesis of the cyanide adduct (III). With various other substrates and catalysts, e.e. values of typically 7-17% are obtained.

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