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Asymmetric “Acetylenic” [3+2] Cycloaddition of Nitrones Catalyzed by Cationic Chiral Pd II Lewis Acid
Author(s) -
Honda Kazuya,
Mikami Koichi
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801016
Subject(s) - cycloaddition , enantioselective synthesis , cationic polymerization , catalysis , chemistry , lewis acids and bases , asymmetric induction , ligand (biochemistry) , nitrone , chiral lewis acid , combinatorial chemistry , organic chemistry , medicinal chemistry , receptor , biochemistry
Highly enantioselective [3+2] cycloaddition of ynones and nitrones has been developed. Very bulky ligand, DTBM‐SEGPHOS, was used for an effective asymmetric induction over distal reaction centers on the linear ynone dipolarophile and for prevention of Pd II catalyst deactivation by coordination of the nitrones. The reaction has wide scope of substrates in both ynones and nitrones.