Synthesis of Chiral Piperazines via Hydrogenation of Pyrazines Activated by Alkyl Halides

• Published in: Organic letters Vol. 18; no. 13; pp. 3082 - 3085
• Main Authors: Huang, Wen-Xue, Liu, Lian-Jin, Wu, Bo, Feng, Guang-Shou, Wang, Baomin, Zhou, Yong-Gui
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.07.2016; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; CATALYZED ASYMMETRIC HYDROGENATION; ENANTIOSELECTIVE REDUCTION; QUINOLINES; PYRIDINIUM SALTS; HETEROAROMATIC-COMPOUNDS; QUINOXALINES; DERIVATIVES; NK1 RECEPTOR ANTAGONIST; HIV PROTEASE INHIBITOR; ISOQUINOLINIUM SALTS

A facile method has been developed for the synthesis of chiral piperazines through Ir-catalyzed hydrogenation of pyrazines activated by alkyl halides, giving a wide range of chiral piperazines including 3-substituted as well as 2,3- and 3,5-disubstituted ones with up to 96% ee. The high enantioselec...