Download PDF
Synthesis 2000; 2000(6): 784-788
DOI: 10.1055/s-2000-6270
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

An Efficient Method for the Preparation of Enantiomerically Pure N-Acylarylsulfonamides Having an Asymmetric Center at the α-Position: Condensation of Acid Chlorides and Arylsulfonamides Under Solid-Liquid Two-Phase Conditions

Natsuki Ishizuka* , Ken-ichi Matsumura, Kunio Hayashi, Katsunori Sakai, Teruo Yamamori
  • *Shionogi Research Laboratories, Shionogi & Co. Ltd., 12-4, Sagisu 5-chome, Fukushima-ku, Osaka 553-0002, Japan; Fax +81 (6) 64 58 09 87; E-mail: natsuki.ishizuka@shionogi.co.jp
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

A convenient synthetic method for the preparation of enantiomerically pure N-acylarylsulfonamides having an asymmetric center at the α-position of the carbonyl group is described. Chiral phenylacetic acids are first converted to the corresponding acid chlorides, which in turn are condensed with arylsulfonamides in the presence of powdered alkaline hydroxide in CH2Cl2, giving the corresponding N-acylarylsulfonamides with good optical and chemical yields. A more convenient one-pot procedure is also possible.

chiral N-acylarylsulfonamides - chiral phenylacetic acid - racemization - solid-liquid two-phase conditions - powdered alkaline hydroxide

      >