Chen Junjie, Han Xiuling, Lu Xiyan
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry , University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.
Org Lett. 2019 Oct 18;21(20):8153-8157. doi: 10.1021/acs.orglett.9b02412. Epub 2019 Sep 26.
A novel Pd(II)-catalyzed reductive asymmetric cyclization of -tosyl-tethered 1,7-enynes using ethanol as a hydrogen source is reported. This reaction provides facile ways for the synthesis of two types of 1,2,3,4-tetrahydroquinolines possessing a chiral quaternary carbon center in high yields with excellent enantioselectivities. The obtained products can also be converted to other chiral functionalized tetrahydroquinolines efficiently. The procedure involves a palladium-catalyzed intramolecular hydropalladation/1,4-addition or β-heteroatom elimination cascade process.
报道了一种新型的钯（II）催化的以乙醇为氢源的对甲苯磺酰基连接的1,7-烯炔的还原不对称环化反应。该反应为高产率、高对映选择性地合成两种具有手性季碳中心的1,2,3,4-四氢喹啉提供了简便方法。所得产物还可高效转化为其他手性官能化的四氢喹啉。该过程涉及钯催化的分子内氢钯化/1,4-加成或β-杂原子消除级联反应。
