Catalytic Enantioselective γ-Alkylation of Carbonyl
Compounds

doi:10.1055/s-0031-1289345

Synfacts 2011(12): 1343-1343
DOI: 10.1055/s-0031-1289345

Metal-Mediated Synthesis

Catalytic Enantioselective γ-Alkylation of Carbonyl Compounds

Rezensent(en):Paul Knochel, Andreas K. Steib

S. 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

Abstract

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Key words

Suzuki cross-coupling - nickel -

Significance

<P>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.</P>

Comment

<P>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.</P>

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