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

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...

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Bibliographic Details
Published inOrganic 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
LanguageEnglish
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
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Summary: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 enantioselectivity, easy scalability, and concise drug synthesis demonstrate the practical utility.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01190