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Asymmetric Organocatalytic Cascade Reactions with α‐Substituted α,β‐Unsaturated Aldehydes
Author(s) -
Galzerano Patrizia,
Pesciaioli Fabio,
Mazzanti Andrea,
Bartoli Giuseppe,
Melchiorre Paolo
Publication year - 2009
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.200903803
Subject(s) - iminium , enantioselective synthesis , amination , enantiomer , amine gas treating , chemistry , enamine , organocatalysis , organic chemistry , combinatorial chemistry , ion , catalysis
Time to α‐branch out! The first highly enantioselective aminocatalytic activation of α‐substituted α,β‐unsaturated aldehydes is presented. The chiral primary amine 1 selectively activates α‐branched enals toward a well‐defined iminium ion/enamine reaction sequence for both Friedel–Crafts/amination and sulfa‐Michael/amination cascades. The valuable multifunctional products, having two contiguous sterocenters, are isolated in high enantiomeric purity.