Extending the Aminocatalytic HOMO‐Raising Activation Strategy: Where Is the Limit? | Zendy

Arceo Elena | Zendy; Melchiorre Paolo | Zendy

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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).

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