Abstract
A general method to generate umpolung of aldimines with cyanide was developed via the addition of cyanide to aldimines followed by a proton transfer from the carbon atom to the nitrogen atom in the resulting cyanide adducts. This novel method was successfully applied to the first imino-Stetter reaction of aldimines obtained from 2-aminocinnamic acid derivatives and aromatic aldehydes with cyanide, affording 2-aryl-substituted indole-3-acetic acid derivatives. Furthermore, the usefulness of this method was successfully demonstrated by the synthesis of an FPTase inhibitor, one of the biologically important 2-arylindole-3-acetic acid derivatives. (Figure presented.).
Original language | English |
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Pages (from-to) | 1566-1570 |
Number of pages | 5 |
Journal | Advanced Synthesis and Catalysis |
Volume | 358 |
Issue number | 10 |
DOIs | |
Publication status | Published - 2016 May 19 |
Keywords
- 2-arylindole-3-acetic acid derivatives
- aldimines
- cyanide
- imino-Stetter reaction
- umpolung
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry