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Extending the Aminocatalytic HOMO‐Raising Activation Strategy: Where Is the Limit?
Author(s) -
Arceo Elena,
Melchiorre Paolo
Publication year - 2012
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.201201347
Subject(s) - trifluoroacetic acid , stereocenter , raising (metalworking) , catalysis , limit (mathematics) , chemistry , amine gas treating , combinatorial chemistry , organic chemistry , materials science , mathematics , enantioselective synthesis , mathematical analysis , metallurgy
Increasingly remote stereocenters are being targeted in asymmetric aminocatalysis. Application of the HOMO‐raising activation concept to δ,δ‐disubstituted 2,4‐dienones confirms the powerful potential of the trienamine strategy. A cinchona‐based primary amine catalyst enables the extension of this activation mode to a highly selective asymmetric Diels–Alder reaction of enones with electron‐deficient dienophiles (see scheme; TFA: trifluoroacetic acid).