A controllable diastereoselective C(sp2)-C(sp3) Negishi coupling reaction of secondary benzylic zinc reagents with aryl bromides has been demonstrated for the first time, forming medicinally important 1-arylphenylethy...A controllable diastereoselective C(sp2)-C(sp3) Negishi coupling reaction of secondary benzylic zinc reagents with aryl bromides has been demonstrated for the first time, forming medicinally important 1-arylphenylethylamines. In the presence of Pd(OAc) 2 and S-phos, open-chain (2-amido-1-phenylethyl)zinc reagents bearing a -NHAc or NHCHO group underwent cross-coupling reaction to give syn 1-arylphenylethylamine as the major products, whereas the zinc reagents bearing a sterically hindered-NHCOC(CH3)2 OTBS group specifically yielded anti 1-arylphenylethylamines.展开更多
A new synthetic route of almotriptan was described. The application of Negishi coupling reaction simpli- fied the process and significantly improved the yield. The synthetic route was also expected to be general for t...A new synthetic route of almotriptan was described. The application of Negishi coupling reaction simpli- fied the process and significantly improved the yield. The synthetic route was also expected to be general for the synthesis of other tryptamines like sumatriptan and avitriptan.展开更多
基金the National Natural Science Foundation of China (21172227)Jishou University (2012)
文摘A controllable diastereoselective C(sp2)-C(sp3) Negishi coupling reaction of secondary benzylic zinc reagents with aryl bromides has been demonstrated for the first time, forming medicinally important 1-arylphenylethylamines. In the presence of Pd(OAc) 2 and S-phos, open-chain (2-amido-1-phenylethyl)zinc reagents bearing a -NHAc or NHCHO group underwent cross-coupling reaction to give syn 1-arylphenylethylamine as the major products, whereas the zinc reagents bearing a sterically hindered-NHCOC(CH3)2 OTBS group specifically yielded anti 1-arylphenylethylamines.
基金Supported by the National Natural Science Foundation of China（Nos.81373259, 81102324）.
文摘A new synthetic route of almotriptan was described. The application of Negishi coupling reaction simpli- fied the process and significantly improved the yield. The synthetic route was also expected to be general for the synthesis of other tryptamines like sumatriptan and avitriptan.
