Nickel-catalyzed asymmetric negishi cross-couplings of secondary allylic chlorides with alkylzincs.
Complementing previous advances in allylation chemistry, an effective nickel/Pybox catalyst for regioselective asymmetric Negishi cross-couplings of racemic secondary allylic chlorides with readily available organozinc halides has been developed. The method has been applied in two key steps of a formal total synthesis of fluvirucinine A1.
Son
Sunghee
S
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Fu
Gregory C
GC
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000475:Alkenes; D006843:Hydrocarbons, Chlorinated; D007769:Lactams; D009942:Organometallic Compounds; C526622:fluvirucinine A1; D009532:Nickel; D015032:Zinc