Kohari Yoshihito, Okuyama Yuko, Kwon Eunsang, Furuyama Taniyuki, Kobayashi Nagao, Otuki Teppei, Kumagai Jun, Seki Chigusa, Uwai Koji, Dai Gang, Iwasa Tatsuo, Nakano Hiroto
Department of Bioengineering, Graduate School of Engineering, Muroran Institute of Technology , 27-1 Mizumoto, Muroran 050-8585, Japan.
J Org Chem. 2014 Oct 17;79(20):9500-11. doi: 10.1021/jo501433c. Epub 2014 Oct 9.
The enantioselective Diels-Alder reaction of 1,2-dihydropyridines with aldehydes using an easily prepared optically active β-amino alcohol catalyst was found to provide optically active isoquinuclidines, an efficient synthetic intermediate of pharmaceutically important compounds such as oseltamivir phosphate, with a satisfactory chemical yield and enantioselectivity (up to 96%, up to 98% ee). In addition, the obtained highly optically pure isoquinuclidine was easily converted to an optically active piperidine having four successive carbon centers.
使用易于制备的旋光性β-氨基醇催化剂，1,2-二氢吡啶与醛的对映选择性狄尔斯-阿尔德反应被发现可提供旋光性异喹核碱，它是诸如磷酸奥司他韦等药学重要化合物的有效合成中间体，具有令人满意的化学产率和对映选择性（高达96%，高达98% ee）。此外，所获得的高光学纯度异喹核碱可轻松转化为具有四个连续碳中心的旋光性哌啶。
