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Bifunctional Brønsted Base Catalyzed Mannich Reaction of β‐Alkoxy α‐Keto Amides: Stereocontrolled Entry to Functionalized Amino Diols
Author(s) -
Echave Haizea,
Bastida Iñaki,
López Rosa,
Palomo Claudio
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802550
Subject(s) - alkoxy group , squaramide , bifunctional , enantioselective synthesis , chemistry , catalysis , mannich reaction , base (topology) , adduct , organic chemistry , organocatalysis , combinatorial chemistry , mathematics , mathematical analysis , alkyl
The potential of β‐alkoxy α‐keto amides as pronucleophiles in the enantioselective Mannich type reaction with p ‐nosyl imines is presented. The proper combination of β‐alkoxy α‐keto amides and a squaramide‐based Brønsted base catalyst produced highly enantioenriched Mannich adducts, which may be transformed into functionalized amino diols.