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Synfacts 2013; 9(1): 0073
DOI: 10.1055/s-0032-1317780
DOI: 10.1055/s-0032-1317780
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Negishi Reaction of Racemic Benzylic Bromides and Alkylzinc Reagents
Binder JT, Cordier CJ, Fu GC * Massachusetts Institute of Technology, Cambridge and California Institute of Technology,
Pasadena, USA
Catalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic Bromides with Achiral Alkylzinc Reagents.
J. Am. Chem. Soc. 2012;
134: 17003-17006
Catalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic Bromides with Achiral Alkylzinc Reagents.
J. Am. Chem. Soc. 2012;
134: 17003-17006
Further Information
Publication History
Publication Date:
17 December 2012 (online)
Significance
Reported here is an enantioselective cross-coupling of racemic benzylic bromides with achiral alkylzinc reagents. A novel bidentate oxazoline-type ligand was developed, leading to the desired products in good yield and enantioselectivity.
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Comment
It is surprising that both reagents are achiral. For acyclic alkylzinc reagents, an usual isomerization was observed and a substantial amount of a branched product was generated from an unbranched nucleophile.
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