Peer-Reviewed Journal Details
Mandatory Fields
M. Kissane, D. Lynch, J. Chopra, S.E. Lawrence, A.R. Maguire;
2008
May
Tetrahedron: Asymmetry
Investigation of the chemoselective and enantioselective oxidation of alpha-thio-beta-chloroacrylamides
Validated
WOS: 13 ()
Optional Fields
19
10
1256
1273
An investigation of the chemoselective and enantioselective oxidation of alpha-thio-beta-chloroacrylamides is described. The alpha-thio-beta-chloroacrylamides can be selectively oxidised to either the racemic sulfoxide or the sulfone very efficiently. The asymmetric sulfur oxidation of alpha-thio-beta-chloroacrylamides is also discussed, with sulfoxide enantioselectivities 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. (C) 2008 Elsevier Ltd. All rights reserved..
10.1016/j.tetasy.2008.04.033
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