高等学校化学研究 ›› 2013, Vol. 29 ›› Issue (4): 678-681.doi: 10.1007/s40242-013-3057-z
Stereoselective Palladium-catalyzed Cross-coupling of (2-Amido-1-phenylpropyl)zinc Compounds with Aryl Bromides
TANG Shi1,2, ZHOU Dong1, LI Shu-hua1, WANG Nai-xing2
- 1. College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P. R. China;
2. Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China
Stereoselective Palladium-catalyzed Cross-coupling of (2-Amido-1-phenylpropyl)zinc Compounds with Aryl Bromides
TANG Shi1,2, ZHOU Dong1, LI Shu-hua1, WANG Nai-xing2
- 1. College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P. R. China;
2. Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China
摘要：
A controllable diastereoselective C(sp2)―C(sp3) Negishi coupling reaction of secondary benzylic zinc reagents with aryl bromides to form medicinally important 2-arylphenylethylamines was demonstrated. In the presence of Pd(OAc)2 and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl(S-phos), open-chain(2-amido-1-phenylethyl)zinc reagent bearing a β-NHAc or NHCHO group undergoes coupling reaction to give syn-1-arylphenylethylamine mainly, whereas the zinc reagent bearing a sterically hindered β-amido group, for example NHCOC(CH3)2OTBS undergoes the coupling reaction to yield anti-1-arylphenylethylamines with a configuration inversion. In addition, a working mechanism for the stereoselective Negishi cross-coupling was also proposed.