Volume 27, Issue 11
Preparative Organic Chemistry
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ChemInform Abstract: Highly Efficient Enantioselective Pauson-Khand Reactions.

A. M. HAY

A. M. HAY

Dep. Pure Appl. Chem., Univ. Strathclyde, Glasgow G1 1XL, UK

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W. J. KERR

W. J. KERR

Dep. Pure Appl. Chem., Univ. Strathclyde, Glasgow G1 1XL, UK

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G. G. KIRK

G. G. KIRK

Dep. Pure Appl. Chem., Univ. Strathclyde, Glasgow G1 1XL, UK

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D. MIDDLEMISS

D. MIDDLEMISS

Dep. Pure Appl. Chem., Univ. Strathclyde, Glasgow G1 1XL, UK

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First published: March 12, 1996

Abstract

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ChemInform Abstract

A range of cobalt-alkyne complexes containing the chiral ligand (II) are synthesized. The diastereomers thus obtained are separated chromatographically. The isolated, optically pure diastereomeric complexes are employed in intermolecular Pauson-Khand reactions using N-methylmorpholine N-oxide as promotor to give high yields of cyclopentenone products such as (IV) from (III) in excellent enantiomeric excesses. Examples are also given with norbornadiene and the reactions with both alkenes proceed to give only the exo- cyclopentenone products.

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