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- Title
DDQ-Promoted Mild and Efficient Metal-Free Oxidative α-Cyanation of N-Acyl/Sulfonyl 1,2,3,4-Tetrahydroisoquinolines.
- Authors
Kim, Hong Pyo; Yu, Heesun; Kim, Hyoungsu; Kim, Seok-Ho; Lee, Dongjoo; Dembinski, Roman
- Abstract
A mild and highly efficient metal-free oxidative α-cyanation of N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines (THIQs) has been accomplished at an ambient temperature via DDQ oxidation and subsequent trapping of N-acyl/sulfonyl iminium ions with (n-Bu)3SnCN. Employing readily removable N-acyl/sulfonyl groups as protecting groups rather than N-aryl ones enables a wide range of applications in natural product synthesis. The synthetic utility of the method was illustrated using a short and efficient formal total synthesis of (±)-calycotomine in three steps.
- Subjects
ISOQUINOLINE synthesis; BENZOQUINONES; QUINONE synthesis; OXIDATION; CYANIDE process; SULFONYL group; OXIDATIVE coupling
- Publication
Molecules, 2018, Vol 23, Issue 12, p3223
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules23123223