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Synfacts 2014; 10(8): 0883
DOI: 10.1055/s-0034-1378458
DOI: 10.1055/s-0034-1378458
Polymer-Supported Synthesis
Asymmetric Allylation of Ketones Using a Titanium–BINOLate Complex
Yadav J, Stanton GR, Fan X, Robinson JR, Schelter EJ, Walsh PJ, * Pericàs MA. * University of Pennsylvania, Philadelphia, USA; Institute of Chemical Research of Catalonia,
Tarragona and Universitat de Barcelona, Spain
Asymmetric Allylation of Ketones and Subsequent Tandem Reactions Catalyzed by a Novel Polymer-Supported Titanium–BINOLate Complex.
Chem. Eur. J. 2014;
20: 7122-7127
Asymmetric Allylation of Ketones and Subsequent Tandem Reactions Catalyzed by a Novel Polymer-Supported Titanium–BINOLate Complex.
Chem. Eur. J. 2014;
20: 7122-7127
Further Information
Publication History
Publication Date:
18 July 2014 (online)
Significance
Polystyrene-supported BINOL 1 was prepared by mixing ethynyl-functionalized BINOL and azidomethylpolystyrene in the presence of copper iodide and DIPEA. The titantium–1 complex generated in situ catalyzed the asymmetric allylation of ketones with tetraallyltin in the presence of 2-propanol to afford the corresponding homoallylic alcohols with up to 95% ee.
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Comment
In the reaction of 3′-methylacetophenone with tetraallyltin, the catalyst was separated by filtration and reused twice with a slight loss of catalytic activity (fresh: 96% yield, 95% ee; 2nd reuse: 90% yield, 82% ee).
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