142635-28-7Relevant articles and documents
Stereoselective Reactions of Lithio-vinylsulfoxides with Aldehydes
Fawcett, John,House, Stuart,Jenkins, Paul R.,Lawrence, Nicholas J.,Russell, David R.
, p. 67 - 74 (2007/10/02)
A series of homochiral vinyl sulfoxides-synthesised by treating vinyl Grignard reagents with homochiral menthyl toluene-p-sulfinate or sulfinyl oxazolidinones 8a and 9a- were deprotonated with LDS and allowed to react with acetaldehyde, isobutyraldehyde, and trimethylacetaldehyde to give β-hydroxy sulfoxides with moderate diastereoselectivity.The sulfoxide 1 gave the best selectivity with the larger aldehydes.The same diastereoselectivity, within experimental error, is observed in the reactions with trimethylacetaldehyde of both E-1 and Z-1 giving 85:15 and 84:16 mixtures of 2c and 3c respectively; evidently, the geometry of the vinyl group does not affect the selectivity.