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Enantiodivergent Brucine Diol‐Catalyzed 1,3‐Dipolar Cycloaddition of Azomethine Ylides with α,β‐Unsaturated Ketones
Author(s) -
Li JianYuan,
Kim Hun Young,
Oh Kyungsoo
Publication year - 2016
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.201500958
Subject(s) - brucine , chemistry , catalysis , cycloaddition , absolute configuration , diol , ligand (biochemistry) , stereochemistry , enantioselective synthesis , 1,3 dipolar cycloaddition , medicinal chemistry , organic chemistry , biochemistry , receptor , strychnine
Enantiodivergent catalyst systems were developed using metals with different ionic radii and a multifunctional brucine diol (BD) ligand. The catalytic use of purported 1:1 Cu‐BD complexes in the 1,3‐dipolar cycloaddition of azomethine ylides with chalcones resulted in the selective formation of endo ‐pyrrolidines in 87–96% ee s with an absolute stereochemical outcome of (2 R ,3 S, 4 R, 5 S ). In contrast, an opposite absolute stereochemical outcome was observed by using the catalysts derived from Ag(I) salts and BD. The demonstration of enantiodivergent approaches to a broad class of substrates/reaction types underlines their synthetic value in asymmetric synthesis.