Volume 27, Issue 18
Preparative Organic Chemistry
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ChemInform Abstract: Gas-Phase Catalytic Asymmetric Reaction Using Chirally Modified Microporous Catalysts.

S. FEAST

S. FEAST

Dep. Chem., Univ. Liverpool, Liverpool L69 3BX, UK

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D. BETHELL

D. BETHELL

Dep. Chem., Univ. Liverpool, Liverpool L69 3BX, UK

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P. C. B. PAGE

P. C. B. PAGE

Dep. Chem., Univ. Liverpool, Liverpool L69 3BX, UK

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F. KING

F. KING

Dep. Chem., Univ. Liverpool, Liverpool L69 3BX, UK

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C. H. ROCHESTER

C. H. ROCHESTER

Dep. Chem., Univ. Liverpool, Liverpool L69 3BX, UK

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M. R. H. SIDDIQUI

M. R. H. SIDDIQUI

Dep. Chem., Univ. Liverpool, Liverpool L69 3BX, UK

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D. J. WILLOCK

D. J. WILLOCK

Dep. Chem., Univ. Liverpool, Liverpool L69 3BX, UK

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G. J. HUTCHINGS

G. J. HUTCHINGS

Dep. Chem., Univ. Liverpool, Liverpool L69 3BX, UK

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First published: April 30, 1996

Abstract

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ChemInform Abstract

It is shown that the dehydration of 2-butanol with a modified zeolite instead of a normal zeolite gives alkenes such as (II)-(IV) under milder conditions. A similar experiment with a zeolite, modified with the (R)-enantiomer of 1,3-dithiane 1-oxide, shows clearly a preference in the reaction of (S)-butan-2-ol over its (R)-enantiomer in the dehydration reaction of the racemic 2-butanol. This first example of an enantioselective gas-phase reaction on a modified heterogeneous catalyst may be of more general interest. Some mechanistical aspects are discussed using computer simulation studies.

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