Saito Kodai, Miyashita Hiromitsu, Akiyama Takahiko
Department Chemistry, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan.
Chem Commun (Camb). 2015 Dec 4;51(93):16648-51. doi: 10.1039/c5cc06436h. Epub 2015 Oct 1.
A chiral Brønsted acid catalyzed dehydrogenative kinetic resolution of tetrahydroquinoline derivatives, which are representative of cyclic secondary amines, based on their hydrogen transfer to aromatic imines was efficiently achieved with high enantioselectivities. This hydrogen transfer of tetrahydroquinolines to imines was not driven by their aromatization to quinolines. This dehydrogenative kinetic resolution could be also applied to the asymmetric synthesis of various benzofused heterocycles containing secondary amine cores.
基于四氢喹啉衍生物向芳香亚胺的氢转移，在手性布朗斯特酸催化下，对作为环状仲胺代表的四氢喹啉衍生物进行脱氢动力学拆分，能够高效实现且具有高对映选择性。四氢喹啉向亚胺的这种氢转移并非由其芳构化为喹啉所驱动。这种脱氢动力学拆分也可应用于各种含仲胺核心的苯并稠合杂环的不对称合成。
