Download PDF
Synlett 2001; 2001(12): 1941-1943
DOI: 10.1055/s-2001-18776
letter
© 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.

NH4OH-promoted Crystallization Induced Dynamic Resolution of N-(S)-(1-Phenylethyl)-α-chloro-α-aryl Acetamides for Asymmetric Syntheses of α-Mercapto Carboxylic Acid Derivatives

Sang-kuk Lee* , Sun Young Lee, Yong Sun Park
  • *Department of Chemistry, Konkuk University, Seoul 143-701, Korea; Fax: + 82(2)34365382; E-mail: parkyong@kkucc.konkuk.ac.kr
Further Information

Publication History

Publication Date:
04 December 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

NH4OH promoted crystallization induced dynamic resolution (CIDR) of configurationally labile α-chloro acetamides has been investigated. CIDR of N-(S)-(1-phenylethyl)-α-chloro-α-aryl acetamides 2-4 has been successfully used for the asymmetric preparation of α-chloro carbonyl functionality up to 97 : 3 diastereomeric ratio in 95% yield. As an application of this methodology we have shown a stereospecific substitution reaction of (αS)-2 with KSAc for the asymmetric preparation of α-mercapto carboxylic acid derivative (αR)-5.

asymmetric synthesis - chiral auxiliaries - kinetic resolution - carboxylic acids - thiols

      >