643734-36-5Relevant academic research and scientific papers
Ligand-mediated enantioselective synthesis of acyclic pyrrole carbinols
Dixon, Darren J.,Scott, Mark S.,Luckhurst, Chris A.
, p. 2420 - 2424 (2005)
The enantioselective synthesis of acyclic pyrrole carbinols via ligand-mediated addition of lithium pyrrolate to aldehydes, and subsequent exploitation of the resulting stereocentre as a stereodirecting group in syn- or anti-selective 1,3-reductions of ketone functionality in the parent aldehyde is described. Georg Thieme Verlag Stuttgart.
Ligand-mediated enantioselective addition of lithium carbazolates to aldehydes
Scott, Mark S.,Lucas, Amanda C.,Luckhurst, Chris A.,Prodger, Jeremy C.,Dixon, Darren J.
, p. 1313 - 1327 (2006)
The enantioselective synthesis of acyclic pyrrole, indole and other N-carbazole carbinols via ligand-mediated addition of lithium carbazolates to aldehydes, together with studies into their catalytic enantioselective synthesis using substoichiometric base and ligand, are reported. The subsequent exploitation of the resulting stereocentre as a controlling element in 1,3-syn- and anti-selective reduction of β-ketones and elaboration to homoallylic alcohols is also described. The Royal Society of Chemistry 2006.
A New Chemoselective Base-Mediated Protection/Deprotection Method for Aldehydes
Dixon, Darren J.,Scott, Mark S.,Luckhurst, Chris A.
, p. 2317 - 2320 (2007/10/03)
A wide range of aldehydes was efficiently protected as pyrrole carbinol derivatives by direct addition of lithium pyrrolate in THF at -78°C. The protection is chemoselective towards aldehydes over ketones and the O-lithiated, O-protonated or O-silylated carbinols may be used to block the aldehyde from nucleophilic and basic reagents at low temperatures. Mild, basic deprotection using DBU, NaOMe or TBAF allows for in situ trapping-reactions (such as Wadsworth-Horner-Emmons olefination) of the released aldehyde.
