1017590-53-2Relevant articles and documents
Enantiopure 2-aryl-2-methyl cyclopentanones by an asymmetric chelation-controlled Heck reaction using aryl bromides: increased preparative scope and effect of ring size on reactivity and selectivity
Datta, Gopal K.,Nordeman, Patrik,Dackenberg, Jakob,Nilsson, Peter,Hallberg, Anders,Larhed, Mats
, p. 1120 - 1126 (2008)
Quaternary 2-aryl-2-methyl cyclopentanones were obtained in 85-94% ee via Pd(0)-catalyzed chelation-controlled asymmetric arylation of a cyclopentenyl ether with aryl bromides and subsequent hydrolysis. Two new cyclohexenyl ethers were synthesized and evaluated as Heck substrates with both aryl iodides and bromides under different reaction conditions. Arylations of the six-membered vinyl ether 1-methyl-2-(S)-(cyclohex-1-enyloxymethyl)-pyrrolidine with aryl bromides were achieved with t-Bu3P-promoted palladium catalysis using either classical or microwave heating. Isolated Heck products were also obtained in high diastereoselectivities (94-98% de).
High stereoselectivity in chelation-controlled intermolecular Heck reactions with aryl chlorides, vinyl chlorides and vinyl triflates
Datta, Gopal K.,Larhed, Mats
, p. XX674-676 (2008/09/17)
Highly stereoselective chelation-controlled Pd(0)-catalyzed β-arylations and β-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. This journal is The Royal Society of Chemistry.