Asymmetric synthesis of functionalized trifluoromethyl-substituted pyrrolidines via an organocatalytic domino Michael/Mannich [3+2] cycloaddition

2016 ◽  
Vol 52 (97) ◽  
pp. 14011-14014 ◽  
Author(s):  
Ying Zhi ◽  
Kun Zhao ◽  
Qiang Liu ◽  
Ai Wang ◽  
Dieter Enders

The asymmetric synthesis of highly functionalized pyrrolidine derivatives with three contiguous stereogenic centers and bearing a trifluoromethyl group has been developed through an organocatalytic domino Michael/Mannich [3+2] cycloaddition sequence.




2013 ◽  
Vol 44 (1) ◽  
pp. 115-120 ◽  
Author(s):  
Muhammad Sohail ◽  
Yao-Feng Wang ◽  
Shaoxiang Wu ◽  
Wei Zeng ◽  
Fu-Xue Chen


2021 ◽  
Vol 14 (11) ◽  
pp. 1125
Author(s):  
Everton M. da Silva ◽  
Hérika D. A. Vidal ◽  
Arlene G. Corrêa

Viral infections cause many severe human diseases, being responsible for remarkably high mortality rates. In this sense, both the academy and the pharmaceutical industry are continuously searching for new compounds with antiviral activity, and in addition, face the challenge of developing greener and more efficient methods to synthesize these compounds. This becomes even more important with drugs possessing stereogenic centers as highly enantioselective processes are required. In this minireview, the advances achieved to improve synthetic routes efficiency and sustainability of important commercially antiviral chiral drugs are discussed, highlighting the use of organocatalytic methods.



Author(s):  
Arlene Gonçalves Corrêa ◽  
Everton Machado da Silva ◽  
Herika Danielle Almeida Vidal

Viral infections inflict many serious human diseases, being responsible for remarkably high mortality rates. In this sense, both the academy and the pharmaceutical industry are continuously searching for new compounds with antiviral activity, and in addition, face the challenge of developing greener and more efficient methods to synthesize these compounds. This becomes even more important with drugs possessing stereogenic centers as highly enantioselective processes are required. In this minireview, the advances achieved to improve synthetic routes efficiency and sustainability of important commercially antiviral chiral drugs are discussed, highlighting the use of organocatalytic methods.



Synthesis ◽  
2016 ◽  
Vol 49 (01) ◽  
pp. 167-174
Author(s):  
Ramon Rios ◽  
Kaiheng Zhang ◽  
Marta Meazza ◽  
Anabel Izaga ◽  
Clotilde Contamine ◽  
...  


2002 ◽  
Vol 4 (25) ◽  
pp. 4519-4522 ◽  
Author(s):  
Shin-ichi Watanabe ◽  
Armando Córdova ◽  
Fujie Tanaka ◽  
Carlos F. Barbas


2017 ◽  
Vol 359 (11) ◽  
pp. 1879-1891 ◽  
Author(s):  
Lei Yu ◽  
Xiaoyan Wu ◽  
Mun Jong Kim ◽  
Venkataramasubramanian Vaithiyanathan ◽  
Yidong Liu ◽  
...  


2013 ◽  
Vol 17 (11) ◽  
pp. 1430-1439 ◽  
Author(s):  
Makoto Michida ◽  
Yoshihiro Takayanagi ◽  
Makoto Imai ◽  
Yukito Furuya ◽  
Kenichi Kimura ◽  
...  


Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2876-2880 ◽  
Author(s):  
Ying Zhi ◽  
Kun Zhao ◽  
Carolina von Essen ◽  
Kari Rissanen ◽  
Dieter Enders

The asymmetric synthesis of trifluoromethylated 3,3′-pyrrolidinyl-dispirooxindole derivatives with four contiguous stereogenic centers, including two vicinal spiro-stereocenters, is described. Employing a bifunctional thiourea catalyst, a domino Michael–Mannich [3+2] cycloaddition occurs readily between isatin ketimines and isatin-derived enoates with good yields and very high stereoselectivities, providing a direct entry to the title compounds of potential medical value.



ChemInform ◽  
2016 ◽  
Vol 47 (18) ◽  
Author(s):  
Xin Huang ◽  
Kenny Pham ◽  
Wenbin Yi ◽  
Xiaofeng Zhang ◽  
Cecilia Clamens ◽  
...  


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