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Enantioselective Enolate Protonations: Friedel–Crafts Reactions with α‐Substituted Acrylates
Author(s) -
Sibi Mukund P.,
Coulomb Julien,
Stanley Levi M.
Publication year - 2008
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.200804221
Subject(s) - enantioselective synthesis , friedel–crafts reaction , protonation , pyrrole , tandem , chemistry , catalysis , organic chemistry , ion , materials science , composite material
Templates rule : A Zn(NTf 2 ) 2 / 1 catalyzed tandem Friedel–Crafts alkylation/enantioselective protonation of pyrroles with isoxazolidinone‐derived α‐substituted α,β‐unsaturated imides, provides high levels of rotamer control and enantioselectivity in the tandem sequence, and affords pyrrole derivatives in good‐to‐excellent yields (68–98 %) and enantioselectivities (43–98 % ee ).