Volume 31, Issue 16
Preparative Organic Chemistry
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ChemInform Abstract: Mechanism and Applications of Lithium Amide-Induced Asymmetric Rearrangements of 4-Substituted and 4,4-Disubstituted Cyclopentene Oxides to Cyclopentenols.

David M. Hodgson

David M. Hodgson

Dyson Perrins Lab., Dep. Chem., Univ. Oxford, Oxford OX1 3QY, UK

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Andrew R. Gibbs

Andrew R. Gibbs

Dyson Perrins Lab., Dep. Chem., Univ. Oxford, Oxford OX1 3QY, UK

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Michael G. B. Drew

Michael G. B. Drew

Dyson Perrins Lab., Dep. Chem., Univ. Oxford, Oxford OX1 3QY, UK

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First published: 09 June 2010

Abstract

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ChemInform Abstract

Recent preliminary communications concerning the title reactions are detailed, i. e. the synthesis of optically pure cyclopentenols such as (II), the rearrangement mechanism by means of labeled cyclopentene oxides (III), and the syntheses of a key prostaglandin precursor (V) and of (+)-iridomyrmecin via enantioselective rearrangement of epoxide (IV).

chemical structure image

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