Investigation of the chemoselective and enantioselective oxidation of α-thio-β-chloroacrylamides
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Accepted Version
Date
2008-05-30
Authors
Kissane, Marie
Lynch, Denis
Chopra, Jay
Lawrence, Simon E.
Maguire, Anita R.
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Publisher
Elsevier
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Abstract
Investigation of the chemoselective and enantioselective oxidation of α-thio-β-chloroacrylamides is described. The α-thio-β-chloroacrylamides can be selectively oxidized to either the racemic sulfoxide or the sulfone very efficiently. The asymmetric sulfur oxidation of α-thio-β-chloroacrylamides is also discussed, with sulfoxide enantioselectivites of up to 52% ee achieved using the Kagan oxidation, and up to 71% ee when the Bolm oxidation is employed. While the enantioselectivities achieved are modest, these are among the most highly functionalised sulfides investigated in catalytic asymmetric oxidation, and the resulting enantioenriched sulfoxides have significant synthetic potential.
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Keywords
α-thio-β-chloroacrylamides , Chemoselective , Enantioselective , Kagan oxidation , Bolm oxidation
Citation
KISSANE, M., LYNCH, D., CHOPRA, J., LAWRENCE, S. E. & MAGUIRE, A. R. 2008. Investigation of the chemoselective and enantioselective oxidation of α-thio-β-chloroacrylamides. Tetrahedron: Asymmetry, 19, 1256-1273.
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NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Asymmetry. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrhedron Asymmetry, [19, 10, (30/05/2008)] 10.1016/j.tetasy.2008.04.033