Enantiospecific intramolecular Heck reactions of secondary benzylic ethers.
Enantioenriched methylenecyclopentanes are synthesized by stereospecific, nickel-catalyzed Heck cyclizations of secondary benzylic ethers. The reaction proceeds in high yield and enantiospecificity for benzylic ethers of both π-extended and simple arenes. Ethers with pendant 1,2-disubstituted olefins form trisubstituted olefins with control of both absolute configuration and alkene geometry. Diastereoselective synthesis of a polycyclic furan is demonstrated.
Department of Chemistry, University of California , Irvine, California 92697-2025, United States.
Michael R
MR
Harris
Mikhail O
MO
Konev
Elizabeth R
ER
Jarvo
D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004987:Ethers / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D009532:Nickel; D013237:Stereoisomerism
D001593:Benzyl Compounds; D004987:Ethers; D005663:Furans; D009532:Nickel