Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis

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Donmez S. E., Soydas E., Aydin G., ŞAHİN O., BOZKAYA U., TÜRKMEN Y. E.

ORGANIC LETTERS, vol.21, no.2, pp.554-558, 2019 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 21 Issue: 2
  • Publication Date: 2019
  • Doi Number: 10.1021/acs.orglett.8b03886
  • Journal Name: ORGANIC LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.554-558
  • Hacettepe University Affiliated: Yes

Abstract

A catalytic aza-Nazarov cyclization between 3,4-dihydroisoquinolines and alpha,beta-unsaturated acyl chlorides has been developed to access alpha-methylene-gamma-lactam products in good yields (up to 79%) as single diastereomers. The reactions proceed efficiently when AgOTf is used as an anion exchange catalyst with a 20 mol % loading at 80 degrees C. Computational studies were performed to investigate the reaction mechanism, and the findings support the role of the -TMS group in reducing the reaction barrier of the key cyclization step.