Literature DB >> 27295391

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

Wen-Xue Huang1,2, Lian-Jin Liu1, Bo Wu1, Guang-Shou Feng1, Baomin Wang2, Yong-Gui Zhou1.   

Abstract

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.

Entities:  

Year:  2016        PMID： 27295391     DOI： 10.1021/acs.orglett.6b01190

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  4 in total

1.  Sequential C-H Arylation and Enantioselective Hydrogenation Enables Ideal Asymmetric Entry to the Indenopiperidine Core of an 11β-HSD-1 Inhibitor.

Authors:  Xudong Wei; Bo Qu; Xingzhong Zeng; Jolaine Savoie; Keith R Fandrick; Jean-Nicolas Desrosiers; Sergei Tcyrulnikov; Maurice A Marsini; Frederic G Buono; Zhibin Li; Bing-Shiou Yang; Wenjun Tang; Nizar Haddad; Osvaldo Gutierrez; Jun Wang; Heewon Lee; Shengli Ma; Scot Campbell; Jon C Lorenz; Matthias Eckhardt; Frank Himmelsbach; Stefan Peters; Nitinchandra D Patel; Zhulin Tan; Nathan K Yee; Jinhua J Song; Frank Roschangar; Marisa C Kozlowski; Chris H Senanayake
Journal:  J Am Chem Soc       Date:  2016-11-17       Impact factor: 15.419

2.  Enantioselective Synthesis of α-(Hetero)aryl Piperidines through Asymmetric Hydrogenation of Pyridinium Salts and Its Mechanistic Insights.

Authors:  Bo Qu; Hari P R Mangunuru; Sergei Tcyrulnikov; Daniel Rivalti; Olga V Zatolochnaya; Dmitry Kurouski; Suttipol Radomkit; Soumik Biswas; Shuklendu Karyakarte; Keith R Fandrick; Joshua D Sieber; Sonia Rodriguez; Jean-Nicolas Desrosiers; Nizar Haddad; Keith McKellop; Scott Pennino; Heewon Lee; Nathan K Yee; Jinhua J Song; Marisa C Kozlowski; Chris H Senanayake
Journal:  Org Lett       Date:  2018-02-20       Impact factor: 6.005

3.  Modulating Conformational Preferences by Allylic Strain toward Improved Physical Properties and Binding Interactions.

Authors:  Hongtao Zhao
Journal:  ACS Omega       Date:  2022-03-04

4.  Expedient syntheses of N-heterocycles via intermolecular amphoteric diamination of allenes.

Authors:  Zhishi Ye; Sarju Adhikari; Yu Xia; Mingji Dai
Journal:  Nat Commun       Date:  2018-02-19       Impact factor: 14.919
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.