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Direct Catalytic Asymmetric Aldol Reaction of an α‐Azido Amide
Author(s) -
Weidner Karin,
Sun Zhongdong,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201501607
Subject(s) - aldol reaction , chemistry , amide , moiety , vicinal , substituent , aziridine , catalysis , hydrolysis , substrate (aquarium) , combinatorial chemistry , organic chemistry , ring (chemistry) , oceanography , geology
A direct aldol reaction of an α‐azido 7‐azaindolinylamide, promoted by a Cu‐based cooperative catalyst, is documented. Aromatic aldehydes bearing an ortho substituent exhibited diastereodivergency depending on the nature of the chiral ligands used. Smooth reactions with ynals highlighted the broad substrate scope. A vicinal azido alcohol unit in the product allowed direct access to the corresponding aziridine and facile hydrolysis of the 7‐azaindolinylamide moiety furnished enantioenriched β‐hydroxy‐α‐azido carboxylic acid derivatives.