Volume 32, Issue 7
Preparative Organic Chemistry
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ChemInform Abstract: Dihydroisoquinolinium Salts: Catalysts for Asymmetric Epoxidation.

Philip C. Bulman Page

Philip C. Bulman Page

Dep. Chem., Univ. Technol., Loughborough, Leicestershire LE11 3TU, UK

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Gerasimos A. Rassias

Gerasimos A. Rassias

Dep. Chem., Univ. Technol., Loughborough, Leicestershire LE11 3TU, UK

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David Barros

David Barros

Dep. Chem., Univ. Technol., Loughborough, Leicestershire LE11 3TU, UK

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Donald Bethell

Donald Bethell

Dep. Chem., Univ. Technol., Loughborough, Leicestershire LE11 3TU, UK

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Mark B. Schilling

Mark B. Schilling

Dep. Chem., Univ. Technol., Loughborough, Leicestershire LE11 3TU, UK

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First published: 30 May 2010

Abstract

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ChemInform Abstract

From a range of tested title salts, differing in the counterion and the bulkiness of chiral N-substituents, isopinocampheyl derived salt IPB gives the highest enantioselectivity in epoxidation of phenylcyclohexene (Id). Some of the reaction parameters such as effects of counterion of the catalyst, of solvent system, of temperature, and of catalyst loading are studied with this compound. Several other aryl alkenes (I), (III), (V), and (VII) are epoxidized under optimized conditions to determine the effect of substrate structure.

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