Volume 19, Issue 18
Organoelement Compounds
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ChemInform Abstract: Lanthanides as Lewis-Acid Catalysts in Aldol Addition, Cyanohydrin-Forming, and Oxirane Ring Opening Reactions.

A. E. VOUGIOUKAS

A. E. VOUGIOUKAS

Lab. Synth. Asym., Ass. CNRS, Centre d'Orsay, Univ. Paris-Sud, 91405 Orsay, France

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H. B. KAGAN

H. B. KAGAN

Lab. Synth. Asym., Ass. CNRS, Centre d'Orsay, Univ. Paris-Sud, 91405 Orsay, France

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First published: May 3, 1988

Abstract

The aldehydes or ketones (I) react with trimethylsilyl cyanide (II) or the ketene silyl acetal (V) in the presence of lanthanide trichlorides, producing mixtures of the α-hydroxy nitriles (III) and the α-siloxy derivatives (IV) or of the β-hydroxy/β-siloxy esters (VI) and (VII).

ChemInform Abstract

The aldehydes or ketones (I) react with trimethylsilyl cyanide (II) or the ketene silyl acetal (V) in the presence of lanthanide trichlorides, producing mixtures of the α-hydroxy nitriles (III) and the α-siloxy derivatives (IV) or of the β-hydroxy/β-siloxy esters (VI) and (VII). The yields and ratios strongly depend on the reaction conditions. Propylene oxide (VIII) and (II) form the siloxypropionitrile (IX) under analogous conditions.

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