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Enantioselective Ficini Reaction: Ruthenium/PNNP‐Catalyzed [2+2] Cycloaddition of Ynamides with Cyclic Enones
Author(s) -
Schotes Christoph,
Mezzetti Antonio
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201007753
Subject(s) - ruthenium , cycloaddition , enantioselective synthesis , yield (engineering) , adduct , catalysis , chemistry , chloride , medicinal chemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy
Chiral cyclobuteneamides made easy : Double chloride abstraction from the ruthenium/PNNP complex 1 in the presence of unsaturated β‐keto esters 2 gives the dicationic adducts [Ru( 2 )(PNNP)] 2+ ( 3 ) that catalyze the [2+2] cycloaddition of a variety of ynamides 4 to produce cyclobuteneamides 5 with high yield and enantioselectivity (see scheme).