Abstract
Abstract Herein, we report the palladium-catalyzed cyclization reactions of indoles bearing a propargyl chloride side chain at their 3-position. In the presence of an external nucleophile, such as a sulfonamide or malonate, indoles bearing a propargyl group at their 3-position gave fused tetracyclic spiroindolines preferentially. However, in the absence of an external nucleophile, the same substrates afforded spiroindoles. Our attempts to develop a catalytic asymmetric spirocyclization onto a propargylpalladium species are also presented in this paper.
| Original language | English |
|---|---|
| Article number | 26723 |
| Pages (from-to) | 6580-6585 |
| Number of pages | 6 |
| Journal | Tetrahedron |
| Volume | 71 |
| Issue number | 37 |
| DOIs | |
| Publication status | Published - 2015 Aug 7 |
Keywords
- Cascade cyclization
- Catalytic asymmetric reaction
- Palladium
- Spiroindole
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Fingerprint Dive into the research topics of 'Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides'. Together they form a unique fingerprint.
Cite this
Iwata, A., Inuki, S., Oishi, S., Fujii, N., & Ohno, H. (2015). Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides. Tetrahedron, 71(37), 6580-6585. [26723]. https://doi.org/10.1016/j.tet.2015.05.006