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Cu(I)‐Ming‐phos Catalyzed Enantioselective [3+2] Cycloadditions of Glycine ketimines to β ‐Trifluoromethyl Enones
Author(s) -
Liu Bing,
Zhang ZhanMing,
Xu Bing,
Xu Shan,
Wu HaiHong,
Zhang Junliang
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800046
Subject(s) - stereocenter , chemistry , enantioselective synthesis , substituent , reactivity (psychology) , glycine , trifluoromethyl , cycloaddition , michael reaction , stereochemistry , catalysis , trifluoromethylation , organocatalysis , medicinal chemistry , combinatorial chemistry , organic chemistry , amino acid , medicine , biochemistry , alkyl , alternative medicine , pathology
A catalytic asymmetric [3+2] cycloaddition of glycine ketimines with β ‐CF 3 β , β ‐disubstituted enones was realized in the presence of a chiral copper(I)/Ming‐Phos complex. This method provides an access to construct highly functionalized pyrrolidines bearing three contiguous stereocenters, which including a trifluoromethylated all‐carbon quaternary stereocenter. The features of this reaction include high chemo‐, diastereo‐, enantioselectivity (up to >20:1 cr, >20:1 dr, 98% ee ), readily available starting materials, well functional‐group tolerance and mild reaction conditions. Control experiments demonstrate that the fluoro‐substituent is crucial for the reactivity.