Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis


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

ORGANIC LETTERS, cilt.21, ss.554-558, 2019 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 21 Konu: 2
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1021/acs.orglett.8b03886
  • Dergi Adı: ORGANIC LETTERS
  • Sayfa Sayıları: ss.554-558

Özet

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.