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Aminocatalytic Enantioselective anti‐ Mannich Reaction of Aldehydes with In Situ Generated N ‐Cbz and N ‐Boc Imines
Author(s) -
Gianelli Chiara,
Sambri Letizia,
Carlone Armando,
Bartoli Giuseppe,
Melchiorre Paolo
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.200803819
Subject(s) - enantioselective synthesis , yield (engineering) , in situ , chemistry , carbamate , amine gas treating , enantiomer , selectivity , catalysis , mannich reaction , combinatorial chemistry , organocatalysis , organic chemistry , enantiomeric excess , materials science , metallurgy
The title reaction catalyzed by the commercially available chiral secondary amine 1 proceeds with high stereocontrol and allows the in situ generation of N‐carbamate‐protected imines from stable α‐amido sulfones 2 . This organocatalytic approach provides easy and convenient access to valuable compounds 3 in high yield, with very good anti selectivity, and in high enantiomeric purity.