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Investigation of ligand loading and asymmetric amplification in CHAOx-catalyzed asymmetric diethylzinc additions

Wipf, P and Pierce, JG and Wang, X (2003) Investigation of ligand loading and asymmetric amplification in CHAOx-catalyzed asymmetric diethylzinc additions. Tetrahedron Asymmetry, 14 (22). 3605 - 3611. ISSN 0957-4166

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Abstract

The recently developed (cyclohexylsulfonylamino)oxazoline (CHAOx) ligand was found to provide high ee's and consistent reaction rates in the asymmetric diethylzinc addition to benzaldehyde over a remarkably large loading range of 0.05-10 mol%. Turnover numbers of 1000-2000 can be explained by the absence of a nonlinear effect and the formation of a catalytically active monomer complex. Substituents at the nitrogen donor atoms of the bidentate ligand prevent zinc-complex dimerization. © 2003 Elsevier Ltd. All rights reserved.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Pierce, JG
Wang, X
Date: 14 November 2003
Date Type: Publication
Journal or Publication Title: Tetrahedron Asymmetry
Volume: 14
Number: 22
Page Range: 3605 - 3611
DOI or Unique Handle: 10.1016/j.tetasy.2003.07.022
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0957-4166
Date Deposited: 18 Jul 2014 21:05
Last Modified: 05 Feb 2019 16:55
URI: http://d-scholarship.pitt.edu/id/eprint/22250

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