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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 13
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Original Articles

Enhancement of Enantioselectivity in the Optical Resolution of Primary Alcohols with Modified Cyclodextrin Colyophilized Lipase

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Pages 2163-2170 | Received 06 Sep 2006, Published online: 03 Jul 2007
 

Abstract

Colyophilization of lipase was carried out with immobilized β‐cyclodextrins (β‐CyD) bearing methyl, acetyl, benzoyl, and nicotinoyl substituents. The colyophilizates enhanced stereoselectivity in the acylation of several alcohols. The enantioselectivity in the acylation of ethyl‐1‐hydroxymethyl‐phenylphosphine oxide using colyophilized lipase with nicotinoyl‐β‐CyD increased approximately threefold (from E=34 to E=113). The amphiphilic character of modified CyDs has been found to influence the enhancement of enantioselectivity.

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