Direct Catalytic Asymmetric Aldol Reaction of an α‐Azido Amide1. Issue 21 (30th March 2015)

• Record Type: Journal Article
• Authors: Weidner, Karin; Sun, Zhongdong; Kumagai, Naoya; Shibasaki, Masakatsu
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 21(2015)
• Page Start: 6236
• Page End: 6240
• Publication Date: 2015-03-30
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201501607
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A direct aldol reaction of an α‐azido 7‐azaindolinylamide, promoted by a Cu‐based cooperative catalyst, is documented. Aromatic aldehydes bearing an <italic>ortho</italic> 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.</p> </abstract>