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Synfacts 2011(12): 1343-1343
DOI: 10.1055/s-0031-1289345
DOI: 10.1055/s-0031-1289345
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Catalytic Enantioselective γ-Alkylation of Carbonyl Compounds
Contributor(s):Paul Knochel, Andreas K. SteibS. L. Zultanski, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings
J. Am. Chem. Soc. 2011, 133: 15362-15364
Massachusetts Institute of Technology, Cambridge, USA
Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings
J. Am. Chem. Soc. 2011, 133: 15362-15364
Further Information
Publication History
Publication Date:
18 November 2011 (online)
Key words
Suzuki cross-coupling - nickel -
Significance
The authors describe a new method for the catalytic enantioselective γ- (and δ-)alkylation of carbonyl compounds by cross-coupling of γ- (and δ-)haloamides with alkylboranes. The reaction is catalyzed by nickel and uses a commercially available chiral diamine ligand to achieve high enantiomeric excess.
Comment
The reaction conditions tolerate alkyl chlorides as well as alkyl bromides as suitable electrophilic cross-coupling partners. Also, an aryl metal, a boronate ester, and a secondary alkyl metal compound are able to undergo the stereoselective cross-coupling with good enantiomeric excess.