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The Role of Binding Constants in the Efficiency of Chiral Catalysts Immobilized by Electrostatic Interactions: The Case of Azabis(oxazoline)–Copper Complexes

✍ Scribed by José M. Fraile; José I. García; Clara I. Herrerías; José A. Mayoral; Oliver Reiser; Antonio Socuéllamos; Heiko Werner

Book ID: 101830754
Publisher: John Wiley and Sons
Year: 2004
Tongue: English
Weight: 175 KB
Volume: 10
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200305739

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✦ Synopsis

Abstract

As shown by theoretical calculations, azabis(oxazoline)–copper complexes are considerably more stable than the analogous bis(oxazoline)–copper complexes. This enhanced stability allows them to be efficiently immobilized by means of electrostatic interactions to different anionic supports, such as clays and nafion–silica nanocomposites, without the loss of a ligand, as is observed for bis(oxazolines). As a result, enantioselectivities of around 90 % ee are obtained in the cyclopropanation reaction between styrene and ethyl diazoacetate. Moreover, the solid catalyst is easily recoverable.

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