Ligand-mediated enantioselective addition of lithium carbazolates to aldehydes.
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 beta-ketones and elaboration to homoallylic alcohols is also described.
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW.
Mark S
MS
Scott
Amanda C
AC
Lucas
Chris A
CA
Luckhurst
Jeremy C
JC
Prodger
Darren J
DJ
Dixon
D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D002227:Carbazoles / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D008024:Ligands; D018020:Lithium Compounds / Q000737:chemistry*; D008958:Models, Molecular; D011758:Pyrroles; D013237:Stereoisomerism
D000438:Alcohols; D000447:Aldehydes; D000588:Amines; D002227:Carbazoles; D008024:Ligands; D018020:Lithium Compounds; D011758:Pyrroles