title: Direct Catalytic Asymmetric Aldol Reaction of an α-Azido Amide.
abstract: 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.
authors.affiliation: Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan).
authors.forename: Karin
authors.initials: K
authors.lastname: Weidner
authors.affiliation: Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan).
authors.forename: Zhongdong
authors.initials: Z
authors.lastname: Sun
authors.affiliation: Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan). nkumagai@bikaken.or.jp.
authors.forename: Naoya
authors.initials: N
authors.lastname: Kumagai
authors.affiliation: Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan). mshibasa@bikaken.or.jp.|JST, ACT-C, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan). mshibasa@bikaken.or.jp.
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000577:Amides; D001386:Azides; D002264:Carboxylic Acids; D003300:Copper; C116609:3-hydroxybutanal
keywords: aldol reaction; amides; asymmetric catalysis; azides; copper