Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides.
This report describes the first enantioselective cross-couplings of racemic secondary benzylic halides, specifically, nickel-catalyzed Negishi reactions of bromides and chlorides. The catalyst components are commercially available and air-stable, and the reaction is not highly oxygen- or moisture-sensitive (it can be set up in the air). The method has been applied to the catalytic enantioselective synthesis of intermediates employed by others in the generation of bioactive compounds (e.g., trikentrin A and an androgen receptor agonist).
Arp
Forrest O
FO
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Fu
Gregory C
GC
D000478:Alkylation; D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D013237:Stereoisomerism
D001593:Benzyl Compounds; D006842:Hydrocarbons, Brominated