Extending Pummerer reaction chemistry. Application to the oxidative cyclization of indole derivatives

Ken S. Feldman; Daniela Boneva Vidulova

doi:10.1021/ol0493406

Extending Pummerer reaction chemistry. Application to the oxidative cyclization of indole derivatives

Ken S. Feldman
, Daniela Boneva Vidulova

Chemistry

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

50 Scopus citations

Abstract

Matrix presented. Treatment of 2-(phenylsulfinyl)indoles bearing a pendant nucleophile at C(3) with Tf₂O/lutidine triggers a Pummerer-like cyclization to furnish 3,3-spirocyclic-2-(phenylthio)indolenine products, which can, in turn, be hydrolyzed to 3,3-spirocyclic oxindoles.

Original language	English (US)
Pages (from-to)	1869-1871
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	11
DOIs	https://doi.org/10.1021/ol0493406
State	Published - May 27 2004

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0493406

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title = "Extending Pummerer reaction chemistry. Application to the oxidative cyclization of indole derivatives",

abstract = "Matrix presented. Treatment of 2-(phenylsulfinyl)indoles bearing a pendant nucleophile at C(3) with Tf2O/lutidine triggers a Pummerer-like cyclization to furnish 3,3-spirocyclic-2-(phenylthio)indolenine products, which can, in turn, be hydrolyzed to 3,3-spirocyclic oxindoles.",

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AU - Feldman, Ken S.

AU - Vidulova, Daniela Boneva

PY - 2004/5/27

Y1 - 2004/5/27

N2 - Matrix presented. Treatment of 2-(phenylsulfinyl)indoles bearing a pendant nucleophile at C(3) with Tf2O/lutidine triggers a Pummerer-like cyclization to furnish 3,3-spirocyclic-2-(phenylthio)indolenine products, which can, in turn, be hydrolyzed to 3,3-spirocyclic oxindoles.

AB - Matrix presented. Treatment of 2-(phenylsulfinyl)indoles bearing a pendant nucleophile at C(3) with Tf2O/lutidine triggers a Pummerer-like cyclization to furnish 3,3-spirocyclic-2-(phenylthio)indolenine products, which can, in turn, be hydrolyzed to 3,3-spirocyclic oxindoles.

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UR - https://www.scopus.com/pages/publications/2942594590#tab=citedBy

U2 - 10.1021/ol0493406

DO - 10.1021/ol0493406

M3 - Article

C2 - 15151435

AN - SCOPUS:2942594590

SN - 1523-7060

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EP - 1871

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Extending Pummerer reaction chemistry. Application to the oxidative cyclization of indole derivatives

Abstract

All Science Journal Classification (ASJC) codes

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