title: Addition of diethylzinc to dicobalt hexacarbonyl complexes of alpha,beta-acetylenic aldehydes with virtually complete enantioselectivity. A formal synthesis of (+)-incrustoporin.
abstract: [reaction: see text] The addition of diethylzinc to dicobalt hexacarbonyl complexes of acetylenes mediated by (R)-2-piperidino-1,1,2-triphenylethanol takes place with very high enantioselectivity (96-99% ee) to afford the S enantiomers of dicobalt hexacarbonyl complexes of 1-alkynyl-1-propanols. The utility of this process is exemplified by the development of a short, highly enantioselective (99% ee) synthesis of unnatural incrustoporin.
authors.affiliation: Unitat de Recerca en Síntesi Asimètrica, Parc Científic de Barcelona and Departament de Química Orgànica, Universitat de Barcelona, c/Josep Samitier, 1-5, E-08028 Barcelona, Spain.
authors.forename: Montserrat
authors.initials: M
authors.lastname: Fontes
authors.forename: Xavier
authors.initials: X
authors.lastname: Verdaguer
authors.forename: Lluís
authors.initials: L
authors.lastname: Solà
authors.forename: Anton
authors.initials: A
authors.lastname: Vidal-Ferran
authors.forename: Katamreddy Subba
authors.initials: KS
authors.lastname: Reddy
authors.forename: Antoni
authors.initials: A
authors.lastname: Riera
authors.forename: Miquel A
authors.initials: MA
authors.lastname: Pericàs
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D000114:Acetylene / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003035:Cobalt / Q000737:chemistry; D007202:Indicators and Reagents; D008024:Ligands; D009942:Organometallic Compounds / Q000737:chemistry; D012996:Solutions; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000935:Antifungal Agents; D007202:Indicators and Reagents; D008024:Ligands; D009942:Organometallic Compounds; D012996:Solutions; C094022:incrustoporin; D003035:Cobalt; D000114:Acetylene; D015107:4-Butyrolactone; C454811:diethylzinc