The synthesis of chiral β-aryl-α,β-unsaturated amino alcohols via a Pd-catalyzed asymmetric allylic amination.
Chiral β-aryl-α,β-unsaturated amino alcohols were synthesized via a Pd-catalyzed asymmetric allylic amination of 4-aryl-1,3-dioxolan-2-one using planar chiral 1,2-disubstituted ferrocene-based phosphinooxazolines as ligands. Under the optimized reaction conditions, a series of substrates were examined and the products were obtained in good to excellent yields (up to 92%) and enantioselectivities (up to 98% ee) under mild reaction conditions. The desired products were determined to be of (R)-configuration and could subsequently be transformed into compounds with interesting biological activity using simple transformations.
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China.
Mao
M
Quan
Nicholas
N
Butt
Jiefeng
J
Shen
Kaiji
K
Shen
Delong
D
Liu
Wanbin
W
Zhang
D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D005296:Ferrous Compounds / Q000737:chemistry; D008024:Ligands; D000075163:Metallocenes; D010080:Oxazoles / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000475:Alkenes; D000605:Amino Alcohols; D005296:Ferrous Compounds; D008024:Ligands; D000075163:Metallocenes; D010080:Oxazoles; D010165:Palladium; C004998:ferrocene