Asymmetric synthesis of 1,1-diarylalkyl units by a copper hydride catalyzed reduction: differentiation between two similar aryl substituents.
An efficient method for the preparation of enantiomerically enriched 1,1-diarylalkyl units has been developed. The use of copper hydride complexed by the (R)-1-[(S)-2-diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine (Josiphos) ligand effects a highly enantioselective conjugate reduction of beta,beta-diaryl-substituted alpha,beta-unsaturated nitriles with aryl groups of similar steric demand and no secondary coordination site. A range of substrates with meta and para substituents on the aryl group were reduced with good to excellent enantioselectivities (up to 97 % enantiomeric excess (ee)) and this methodology was applied to the formal synthesis of indatraline.
Department of Chemistry and Institute of Basic Science, Sungkyunkwan University, Suwon 440-746, Korea.
Kihyun
K
Yoo
Hyohyun
H
Kim
Jaesook
J
Yun
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007189:Indans / Q000138:chemical synthesis / Q000737:chemistry; D008744:Methylamines / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
D007189:Indans; D008744:Methylamines; D009570:Nitriles; D012821:Silanes; C418119:indatraline; D003300:Copper