Copper(I)-Catalyzed Enantio- and Diastereoselective Tandem Reductive Aldol Reaction

Copper(I)-Catalyzed Enantio- and Diastereoselective Tandem Reductive Aldol Reaction

An efficient method for the enantioselective tandem reductive aldol reaction of methyl acrylate with aldehydes is reported. By using a copper(I) precursor and a proper diphosphane ligand, high reactivities can be reached, with TOF up to 40 000 h-1. Taniaphos-based ligands lead to enantioselectivitie...

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Veröffentlicht in:Organic letters 2006-12, Vol.8 (26), p.5943-5946
Hauptverfasser: Chuzel, Olivier, Deschamp, Julia, Chausteur, Christophe, Riant, Olivier
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Catalysis
Chemical Sciences
Copper - chemistry
Ligands
Organic chemistry
Stereoisomerism
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Zusammenfassung:An efficient method for the enantioselective tandem reductive aldol reaction of methyl acrylate with aldehydes is reported. By using a copper(I) precursor and a proper diphosphane ligand, high reactivities can be reached, with TOF up to 40 000 h-1. Taniaphos-based ligands lead to enantioselectivities of up to 97% in the case of the major syn diastereoisomer.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062398v