Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides

Akira Iwata; Shinsuke Inuki; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno

doi:10.1016/j.tet.2015.05.006

Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides

Akira Iwata, Shinsuke Inuki, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

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	https://doi.org/10.1016/j.tet.2015.05.006
Publication status	Published - 2015 Aug 7

Keywords

Cascade cyclization
Catalytic asymmetric reaction
Palladium
Spiroindole

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2015.05.006

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title = "Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides",

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.",

keywords = "Cascade cyclization, Catalytic asymmetric reaction, Palladium, Spiroindole",

author = "Akira Iwata and Shinsuke Inuki and Shinya Oishi and Nobutaka Fujii and Hiroaki Ohno",

note = "Funding Information: This work was supported by a Grant-in-Aid for the Encouragement of Young Scientists (A) from JSPS, Japan; Platform for Drug Design, Discovery, and Development from MEXT, Japan; research Grants from Takeda Science Foundation . A.I. and S.I. are grateful for Research Fellowships from the Japan Society for the Promotion of Science (JSPS) for Young Scientists. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

month = aug,

day = "7",

doi = "10.1016/j.tet.2015.05.006",

language = "English",

volume = "71",

pages = "6580--6585",

journal = "Tetrahedron",

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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

N1 - Funding Information: This work was supported by a Grant-in-Aid for the Encouragement of Young Scientists (A) from JSPS, Japan; Platform for Drug Design, Discovery, and Development from MEXT, Japan; research Grants from Takeda Science Foundation . A.I. and S.I. are grateful for Research Fellowships from the Japan Society for the Promotion of Science (JSPS) for Young Scientists. Publisher Copyright: © 2015 Elsevier Ltd.

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

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U2 - 10.1016/j.tet.2015.05.006

DO - 10.1016/j.tet.2015.05.006

M3 - Article

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VL - 71

SP - 6580

EP - 6585

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 37

M1 - 26723

ER -

Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides

Abstract

Keywords

ASJC Scopus subject areas

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