Investigation of the chemoselective and enantioselective oxidation of alpha-thio-beta-chloroacrylamides

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TY  - JOUR
  - 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: 12 ()
  - 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
DA  - 2008/05
ER  - 
@article{V723558,
   = {M. Kissane,  D. Lynch and  J. Chopra,  S.E. Lawrence and  A.R. Maguire },
   = {2008},
   = {May},
   = {Tetrahedron: Asymmetry},
   = {Investigation of the chemoselective and enantioselective oxidation of alpha-thio-beta-chloroacrylamides},
   = {Validated},
   = {WOS: 12 ()},
   = {19},
   = {10},
  pages = {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},
  source = {IRIS}
}
AUTHORSM. Kissane, D. Lynch, J. Chopra, S.E. Lawrence, A.R. Maguire
YEAR2008
MONTHMay
JOURNAL_CODETetrahedron: Asymmetry
TITLEInvestigation of the chemoselective and enantioselective oxidation of alpha-thio-beta-chloroacrylamides
STATUSValidated
TIMES_CITEDWOS: 12 ()
SEARCH_KEYWORD
VOLUME19
ISSUE10
START_PAGE1256
END_PAGE1273
ABSTRACTAn 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..
PUBLISHER_LOCATION
ISBN_ISSN
EDITION
URL
DOI_LINK10.1016/j.tetasy.2008.04.033
FUNDING_BODY
GRANT_DETAILS