Addition of diethylzinc to dicobalt hexacarbonyl complexes of alpha,beta-acetylenic aldehydes with virtually complete enantioselectivity. A formal synthesis of (+)-incrustoporin.
[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.
Fontes
Montserrat
M
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.
Verdaguer
Xavier
X
Solà
Lluís
L
Vidal-Ferran
Anton
A
Reddy
Katamreddy Subba
KS
Riera
Antoni
A
Pericàs
Miquel A
MA
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
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