☆ 4.8 Article

Direct Catalytic Asymmetric Aldol Reaction of an -Azido Amide

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

卷 54, 期 21, 页码 6236-6240

出版社

WILEY-V C H VERLAG GMBH

DOI: 10.1002/anie.201501607

关键词

aldol reaction; amides; asymmetric catalysis; azides; copper

类别

Chemistry, Multidisciplinary

资金

JST
ACT-C
KAKENHI from JSPS [25713002]
Grants-in-Aid for Scientific Research [25713002] Funding Source: KAKEN

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Reagent

摘要

A direct aldol reaction of an -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 -hydroxy--azido carboxylic acid derivatives.

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