Regioselective oxidative cleavage of benzylidene acetals: synthesis of α- and β-benzoyloxy carboxylic acids

Kumar, Ponminor Senthil ; Banerjee, Amit ; Baskaran, Sundarababu (2009) Regioselective oxidative cleavage of benzylidene acetals: synthesis of α- and β-benzoyloxy carboxylic acids Angewandte Chemie International Edition, 49 (4). pp. 804-807. ISSN 1433-7851

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.20...

Related URL: http://dx.doi.org/10.1002/anie.200905952

Abstract

Ruthenium has twice the fun: The synthetic potential of the highly regio- and stereoselective title reaction, which relies on two oxidative cleavage steps promoted by RuCl3 in combination with NaIO4 (see example; Bz=benzoyl), was demonstrated with the synthesis of biologically active cis-(2R,3S)-3-hydroxypipecolic acid from D-glucose.

Item Type:Article
Source:Copyright of this article belongs to John Wiley and Sons, Inc.
Keywords:Benzylidene Acetals; Hydroxy Carboxylic Acids; Oxidation; Regioselectivity; Terminal Alkenes
ID Code:100050
Deposited On:27 Nov 2016 13:31
Last Modified:27 Nov 2016 13:31

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