Volume 29, Issue 40
Preparative Organic Chemistry
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ChemInform Abstract: Mixed Aggregates of Lithium Tetramethylpiperidide with Butyllithium: Stereoselectivity of Ketone Enolization.

Y. BALAMRAJU

Y. BALAMRAJU

Dep. Chem., La. Tech. Univ., Ruston, LA 71272, USA

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C. D. SHARP

C. D. SHARP

Dep. Chem., La. Tech. Univ., Ruston, LA 71272, USA

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W. GAMMILL

W. GAMMILL

Dep. Chem., La. Tech. Univ., Ruston, LA 71272, USA

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N. MANUEL

N. MANUEL

Dep. Chem., La. Tech. Univ., Ruston, LA 71272, USA

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L. M. PRATT

L. M. PRATT

Dep. Chem., La. Tech. Univ., Ruston, LA 71272, USA

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First published: 19 June 2010

Abstract

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ChemInform Abstract

The enolization of 3-pentanone by lithium tetramethylpiperidide mixed aggregates with butyllithium is studied and the results are compared to those obtained using lithium tetramethylpiperidide alone. Mixed aggregates result in a slightly higher stereoselectivity which increases with decreasing percent conversion of the lithium base. The results are discussed based on ab initio and semiempirical calculations.

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