Ligand-mediated enantioselective addition of lithium carbazolates to aldehydes.

Journal article

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.

Authors: Scott, MS; Lucas, A; Luckhurst, C; Prodger, J; Dixon, D

• Publication status: Published
• Journal: Organic and biomolecular chemistry
• Volume: 4
• Issue: 7
• Pages: 1313-1327
• Publication date: 2006-04-01
• DOI: 10.1039/b515356e
• EISSN: 1477-0539
• ISSN: 1477-0520
• Language: English
• Keywords: Alcohols; Models, Molecular; Chromatography, High Pressure Liquid; Lithium Compounds; Amines; Pyrroles; Ligands; Carbazoles; Aldehydes; Stereoisomerism