Published January 1, 2019
| Version v1
Journal article
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Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis
Creators
- 1. Bilkent Univ, Dept Chem, Fac Sci, TR-06800 Ankara, Turkey
- 2. Hacettepe Univ, Dept Chem, TR-06800 Ankara, Turkey
- 3. Sinop Univ, Sci & Technol Res Applicat & Res Ctr, TR-57000 Sinop, Turkey
Description
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.
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