Palladium-catalyzed sequential one-pot reaction of aryl bromides with O-homoallylhydroxylamines: synthesis of N-aryl-beta-amino alcohols.
The palladium-catalyzed sequential one-pot N-arylation-carbo-amination-C-arylation of O-homoallylhydroxylamines with two different aryl bromides provides rapid entry to differentially arylated N-aryl-3-arylmethylisoxazolidines in good yields with excellent diastereoselectivity. The obtained isoxazolidines can be reductively cleaved to cis-N-aryl-beta-amino alcohols in short times and in high yields at room temperature.
Peng
Jinsong
J
Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China. chenyw@cioc.ac.cn
Jiang
Dahong
D
Lin
Wenqing
W
Chen
Yuanwei
Y
D000498:Allyl Compounds / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001969:Bromobenzenes / Q000737:chemistry*; D002384:Catalysis; D006898:Hydroxylamines / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D000605:Amino Alcohols; D001969:Bromobenzenes; D006898:Hydroxylamines; D010165:Palladium