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 |
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Keywords
- Cascade cyclization
- Catalytic asymmetric reaction
- Palladium
- Spiroindole
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides. / Iwata, Akira; Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki.
In: Tetrahedron, Vol. 71, No. 37, 26723, 07.08.2015, p. 6580-6585.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides
AU - Iwata, Akira
AU - Inuki, Shinsuke
AU - Oishi, Shinya
AU - Fujii, Nobutaka
AU - Ohno, Hiroaki
PY - 2015/8/7
Y1 - 2015/8/7
N2 - 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.
AB - 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.
KW - Cascade cyclization
KW - Catalytic asymmetric reaction
KW - Palladium
KW - Spiroindole
UR - http://www.scopus.com/inward/record.url?scp=84938749658&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84938749658&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2015.05.006
DO - 10.1016/j.tet.2015.05.006
M3 - Article
AN - SCOPUS:84938749658
VL - 71
SP - 6580
EP - 6585
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 37
M1 - 26723
ER -