Asymmetric 1,4-Reductions of Hindered β-Substituted Cycloalkenones Using Catalytic SEGPHOS−Ligated CuH

Asymmetric 1,4-Reductions of Hindered β-Substituted Cycloalkenones Using Catalytic SEGPHOS−Ligated CuH

The reagent combination of catalytic amounts of copper hydride ligated by a nonracemic SEGPHOS ligand leads in situ to an extremely reactive species capable of effecting asymmetric hydrosilylations of conjugated cyclic enones in very high ees. An unprecedented substrate-to-ligand ratio as high as 27...

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Veröffentlicht in:Organic letters 2004-04, Vol.6 (8), p.1273-1275
Hauptverfasser: Lipshutz, Bruce H, Servesko, Jeff M, Petersen, Tue B, Papa, Patrick P, Lover, Andrew A
Format: Artikel
Sprache:eng
Schlagworte:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Catalysis
Copper - chemistry
Cyclohexanones - chemical synthesis
Cyclohexanones - pharmacology
Ketones - chemistry
Ligands
Molecular Structure
Organosilicon Compounds - chemistry
Oxidation-Reduction
Stereoisomerism
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Zusammenfassung:The reagent combination of catalytic amounts of copper hydride ligated by a nonracemic SEGPHOS ligand leads in situ to an extremely reactive species capable of effecting asymmetric hydrosilylations of conjugated cyclic enones in very high ees. An unprecedented substrate-to-ligand ratio as high as 275 000:1 for this transformation has been documented.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0400185