A copper-catalyzed domino radical cyclization route to benzospiro-indolizidinepyrrolidinones

Christian V. Stevens; Ellen Van Meenen; Kurt G.R. Masschelein; Yves Eeckhout; Wim Hooghe; Bart D'hondt; Victor N. Nemykin; Viktor Zhdankin

doi:10.1016/j.tetlet.2007.07.211

A copper-catalyzed domino radical cyclization route to benzospiro-indolizidinepyrrolidinones

Christian V. Stevens, Ellen Van Meenen, Kurt G.R. Masschelein, Yves Eeckhout, Wim Hooghe, Bart D'hondt, Victor N. Nemykin, Viktor Zhdankin

Chemistry & Biochemistry

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

20 Scopus citations

Abstract

In this Letter the synthesis of benzospiro-indolizidinepyrrolidinones is described by a domino atom transfer radical cyclization reaction using a copper catalyst. The structure of one of the products was established by single crystal X-ray diffraction. The investigated precursors, bearing a homo allyl substituent on the N-indole, result in a 5-exo-trig, followed by a 6-endo-trig cyclization. When the N-indole is substituted with an allyl group, only the spiro-cyclization occurs.

Original language	English (US)
Pages (from-to)	7108-7111
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2007.07.211
State	Published - Oct 1 2007

Bibliographical note

Funding Information:
We are grateful to the Fund of Scientific Research-Flanders (FWO-Vlaanderen) and Ghent University for financial assistance of this research.

Keywords

ATRC
Atom transfer radical cyclization
Cu(I)Cl
Domino reaction

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10.1016/j.tetlet.2007.07.211

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title = "A copper-catalyzed domino radical cyclization route to benzospiro-indolizidinepyrrolidinones",

abstract = "In this Letter the synthesis of benzospiro-indolizidinepyrrolidinones is described by a domino atom transfer radical cyclization reaction using a copper catalyst. The structure of one of the products was established by single crystal X-ray diffraction. The investigated precursors, bearing a homo allyl substituent on the N-indole, result in a 5-exo-trig, followed by a 6-endo-trig cyclization. When the N-indole is substituted with an allyl group, only the spiro-cyclization occurs.",

keywords = "ATRC, Atom transfer radical cyclization, Cu(I)Cl, Domino reaction",

author = "Stevens, {Christian V.} and {Van Meenen}, Ellen and Masschelein, {Kurt G.R.} and Yves Eeckhout and Wim Hooghe and Bart D'hondt and Nemykin, {Victor N.} and Viktor Zhdankin",

note = "Funding Information: We are grateful to the Fund of Scientific Research-Flanders (FWO-Vlaanderen) and Ghent University for financial assistance of this research.",

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doi = "10.1016/j.tetlet.2007.07.211",

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T1 - A copper-catalyzed domino radical cyclization route to benzospiro-indolizidinepyrrolidinones

AU - Stevens, Christian V.

AU - Van Meenen, Ellen

AU - Masschelein, Kurt G.R.

AU - Eeckhout, Yves

AU - Hooghe, Wim

AU - D'hondt, Bart

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor

N1 - Funding Information: We are grateful to the Fund of Scientific Research-Flanders (FWO-Vlaanderen) and Ghent University for financial assistance of this research.

PY - 2007/10/1

Y1 - 2007/10/1

N2 - In this Letter the synthesis of benzospiro-indolizidinepyrrolidinones is described by a domino atom transfer radical cyclization reaction using a copper catalyst. The structure of one of the products was established by single crystal X-ray diffraction. The investigated precursors, bearing a homo allyl substituent on the N-indole, result in a 5-exo-trig, followed by a 6-endo-trig cyclization. When the N-indole is substituted with an allyl group, only the spiro-cyclization occurs.

AB - In this Letter the synthesis of benzospiro-indolizidinepyrrolidinones is described by a domino atom transfer radical cyclization reaction using a copper catalyst. The structure of one of the products was established by single crystal X-ray diffraction. The investigated precursors, bearing a homo allyl substituent on the N-indole, result in a 5-exo-trig, followed by a 6-endo-trig cyclization. When the N-indole is substituted with an allyl group, only the spiro-cyclization occurs.

KW - ATRC

KW - Atom transfer radical cyclization

KW - Cu(I)Cl

KW - Domino reaction

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DO - 10.1016/j.tetlet.2007.07.211

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -

A copper-catalyzed domino radical cyclization route to benzospiro-indolizidinepyrrolidinones

Abstract

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Keywords

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