Synthesis of 3-arylpiperidines by a radical 1,4-aryl migration

Alexandra Gheorghe; Béatrice Quiclet-Sire; Xavier Vila; Samir Z. Zard

doi:10.1021/ol0503642

Synthesis of 3-arylpiperidines by a radical 1,4-aryl migration

Alexandra Gheorghe
, Béatrice Quiclet-Sire
, Xavier Vila
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

60 Citations (Scopus)

Abstract

(Chemical Equation Presented) A route to 3-arylpiperidines, 3-arylpyridines, and 5-arylpiperidin-2-ones involving a radical 1,4-aryl migration has been explored. The sequence requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with dilauroyl peroxide to give the 1,4-aryl transfer product, which upon acidic hydrolysis affords the desired piperidine derivative.

Original language	English
Pages (from-to)	1653-1656
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	8
DOIs	https://doi.org/10.1021/ol0503642
Publication status	Published - 14 Apr 2005
Externally published	Yes

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title = "Synthesis of 3-arylpiperidines by a radical 1,4-aryl migration",

abstract = "(Chemical Equation Presented) A route to 3-arylpiperidines, 3-arylpyridines, and 5-arylpiperidin-2-ones involving a radical 1,4-aryl migration has been explored. The sequence requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with dilauroyl peroxide to give the 1,4-aryl transfer product, which upon acidic hydrolysis affords the desired piperidine derivative.",

author = "Alexandra Gheorghe and B{\'e}atrice Quiclet-Sire and Xavier Vila and Zard, \{Samir Z.\}",

year = "2005",

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doi = "10.1021/ol0503642",

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journal = "Organic Letters",

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T1 - Synthesis of 3-arylpiperidines by a radical 1,4-aryl migration

AU - Gheorghe, Alexandra

AU - Quiclet-Sire, Béatrice

AU - Vila, Xavier

AU - Zard, Samir Z.

PY - 2005/4/14

Y1 - 2005/4/14

N2 - (Chemical Equation Presented) A route to 3-arylpiperidines, 3-arylpyridines, and 5-arylpiperidin-2-ones involving a radical 1,4-aryl migration has been explored. The sequence requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with dilauroyl peroxide to give the 1,4-aryl transfer product, which upon acidic hydrolysis affords the desired piperidine derivative.

AB - (Chemical Equation Presented) A route to 3-arylpiperidines, 3-arylpyridines, and 5-arylpiperidin-2-ones involving a radical 1,4-aryl migration has been explored. The sequence requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with dilauroyl peroxide to give the 1,4-aryl transfer product, which upon acidic hydrolysis affords the desired piperidine derivative.

U2 - 10.1021/ol0503642

DO - 10.1021/ol0503642

M3 - Article

AN - SCOPUS:17844373775

SN - 1523-7060

VL - 7

SP - 1653

EP - 1656

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Synthesis of 3-arylpiperidines by a radical 1,4-aryl migration

Abstract

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