Inoshita Taichi, Goshi Kei, Morinaga Yuka, Umeda Yuhei, Ishikawa Hayato
Department of Chemistry, Graduate School of Science and Technology , Kumamoto University , 2-39-1, Kurokami , Chuo-ku, Kumamoto 860-8555 , Japan.
Faculty of Advanced Science and Technology , Kumamoto University , 2-39-1, Kurokami , Chuo-ku, Kumamoto 860-8555 , Japan.
Org Lett. 2019 Apr 19;21(8):2903-2907. doi: 10.1021/acs.orglett.9b00932. Epub 2019 Apr 5.
A trienamine-mediated asymmetric Diels-Alder reaction using a 5-nitro-2,3-dihydro-4-pyridone derivative as a dienophile in the presence of a secondary amine organocatalyst derived from cis-hydroxyproline was discovered. The reaction provides optically active octahydroquinolines through an endo-selective [4 + 2] cyclization pathway. The following stereoselective denitration, isomerization, and/or hydrogenation generated divergent stereoisomers of decahydroquinolines, which are useful synthons for the total synthesis of Lycopodium alkaloids.
发现了一种由三烯胺介导的不对称狄尔斯-阿尔德反应，该反应使用5-硝基-2,3-二氢-4-吡啶酮衍生物作为亲双烯体，在由顺式羟基脯氨酸衍生的仲胺有机催化剂存在下进行。该反应通过内型选择性[4 + 2]环化途径提供光学活性八氢喹啉。随后的立体选择性脱硝、异构化和/或氢化反应生成了十氢喹啉的不同立体异构体，这些异构体是石松生物碱全合成的有用合成子。
