High stereoselectivity in chelation-controlled intermolecular Heck reactions with aryl chlorides, vinyl chlorides and vinyl triflates.
Highly stereoselective chelation-controlled Pd(0)-catalyzed beta-arylations and beta-vinylations of a five-membered chiral, pyrrolidine-based vinyl ether were achieved using aryl- and vinyl chlorides as substrates, yielding quaternary 2-aryl/vinyl-2-methyl cyclopentanones in 89-96% ee under neutral reaction conditions.
Datta
Gopal K
GK
Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, BMC, Uppsala, Box 574, SE-751 23, Sweden.
Larhed
Mats
M
D002384:Catalysis; D002614:Chelating Agents / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry; D006868:Hydrolysis; D008698:Mesylates / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D014752:Vinyl Chloride / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D002614:Chelating Agents; D004987:Ethers; D008698:Mesylates; D014753:Vinyl Compounds; C437735:vinyl triflate; D010165:Palladium; D014752:Vinyl Chloride