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