Tri- and tetrasubstituted functionalized vinyl sulfides by radical allylation

Laurent Debien; Marie Gabrielle Braun; Béatrice Quiclet-Sire; Samir Z. Zard

doi:10.1021/ol403103u

Tri- and tetrasubstituted functionalized vinyl sulfides by radical allylation

Laurent Debien
, Marie Gabrielle Braun
, Béatrice Quiclet-Sire
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

Abstract

2-Fluoropyridinyl-6-oxy- precursors derived from phenyl vinyl sulfide react with radicals generated from xanthates via an addition-elimination process to furnish the corresponding vinyl sulfides in good yields. This convergent method is operationally simple and enables a straightforward synthesis of the difficult to access tetrasubstituted vinyl sulfides. Vinyl sulfides were used as more robust enol ether surrogates in highly stereoselective reactions with N-acylium cations leading to nitrogen-containing polycyclic structures.

Original language	English
Pages (from-to)	6250-6253
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	24
DOIs	https://doi.org/10.1021/ol403103u
Publication status	Published - 20 Dec 2013
Externally published	Yes

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10.1021/ol403103u

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title = "Tri- and tetrasubstituted functionalized vinyl sulfides by radical allylation",

abstract = "2-Fluoropyridinyl-6-oxy- precursors derived from phenyl vinyl sulfide react with radicals generated from xanthates via an addition-elimination process to furnish the corresponding vinyl sulfides in good yields. This convergent method is operationally simple and enables a straightforward synthesis of the difficult to access tetrasubstituted vinyl sulfides. Vinyl sulfides were used as more robust enol ether surrogates in highly stereoselective reactions with N-acylium cations leading to nitrogen-containing polycyclic structures.",

author = "Laurent Debien and Braun, \{Marie Gabrielle\} and B{\'e}atrice Quiclet-Sire and Zard, \{Samir Z.\}",

year = "2013",

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doi = "10.1021/ol403103u",

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volume = "15",

pages = "6250--6253",

journal = "Organic Letters",

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T1 - Tri- and tetrasubstituted functionalized vinyl sulfides by radical allylation

AU - Debien, Laurent

AU - Braun, Marie Gabrielle

AU - Quiclet-Sire, Béatrice

AU - Zard, Samir Z.

PY - 2013/12/20

Y1 - 2013/12/20

N2 - 2-Fluoropyridinyl-6-oxy- precursors derived from phenyl vinyl sulfide react with radicals generated from xanthates via an addition-elimination process to furnish the corresponding vinyl sulfides in good yields. This convergent method is operationally simple and enables a straightforward synthesis of the difficult to access tetrasubstituted vinyl sulfides. Vinyl sulfides were used as more robust enol ether surrogates in highly stereoselective reactions with N-acylium cations leading to nitrogen-containing polycyclic structures.

AB - 2-Fluoropyridinyl-6-oxy- precursors derived from phenyl vinyl sulfide react with radicals generated from xanthates via an addition-elimination process to furnish the corresponding vinyl sulfides in good yields. This convergent method is operationally simple and enables a straightforward synthesis of the difficult to access tetrasubstituted vinyl sulfides. Vinyl sulfides were used as more robust enol ether surrogates in highly stereoselective reactions with N-acylium cations leading to nitrogen-containing polycyclic structures.

U2 - 10.1021/ol403103u

DO - 10.1021/ol403103u

M3 - Article

AN - SCOPUS:84890949343

SN - 1523-7060

VL - 15

SP - 6250

EP - 6253

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Tri- and tetrasubstituted functionalized vinyl sulfides by radical allylation

Abstract

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