Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 34, Pages 12344-12353Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja904152r
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Funding
- Spanish (Consolider Ingenio) [CSD2006-0003, CTQ2007-62288/BQU 2008PGIR/07, 2008PGIR/08, 2005SGR007777]
- COST [D40]
- Graduate School 1213 of Deutsche Forschungsgemeinschaft
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A modular library of readily available phosphite-oxazoline ligands (L1-L16a-f) has been successfully applied for the first time in the Ir-catalyzed asymmetric hydrogenation of a broad range of highly unfunctionalized 1,1,-disubstituted terminal alkenes. Enantioselectivities up to >99% and full conversions were obtained in several 1, 1 -disubstituted alkenes, including substrate classes that have never been asymmetrically hydrogenated before (i.e,, 1,1-heteoraryl-alkyl, 1,1-diaryl, trifluoromethyl, etc.). The results indicated that these catalytic systems have high tolerance to the steric and electronic requirements of the substrate and also to the presence of a neighboring polar group. The asymmetric hydrogenations were also performed using propylene carbonate as solvent, which allowed the It catalyst to be reused and maintained the excellent enantioselectivities.
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