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Chiral Trifluoromethylated Pyrrolidines via Cu–Catalyzed Asymmetric 1,3‐Dipolar Cycloaddition
Author(s) -
Cheng Xiang,
Yan Dingce,
Dong XiuQin,
Wang ChunJiang
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000295
Subject(s) - stereocenter , chemistry , pyrrolidine , cycloaddition , catalysis , enantioselective synthesis , trifluoromethyl , 1,3 dipolar cycloaddition , yield (engineering) , medicinal chemistry , acrylate , stereochemistry , organic chemistry , combinatorial chemistry , monomer , polymer , metallurgy , alkyl , materials science
An efficient access to chiral pyrrolidine derivatives bearing one trifluoromethylated quaternary stereogenic centers is developed through Cu(I)/( S )‐TF‐BiphamPhos‐catalyzed asymmetric 1,3‐dipolar cycloaddition of azomethine ylides with tert ‐butyl 2‐(trifluoromethyl)acrylate in moderate to high yields, excellent diastereoselectivities and good enantioselectivities (up to 95% yield, >20 : 1 dr, 89% ee).