Tri- and Tetrasubstituted Functionalized Vinyl Sulfides by Radical Allylation

被引：13

作者：

Debien, Laurent ^{[1
]}

Braun, Marie-Gabrielle ^{[1
]}

Quiclet-Sire, Beatrice ^{[1
]}

Zard, Samir Z. ^{[1
]}

机构：

[1] Ecole Polytech, Synth Organ Lab, CNRS, UMR 7652, F-91128 Palaiseau, France

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 24期

关键词：

INTRAMOLECULAR REACTIONS; REDUCTIVE LITHIATION; ALKENYL SULFIDES; ENOL THIOETHERS; CYCLIZATION; HYDROTHIOLATION; ALKYNES; THIOLS; ARYL; AMIDOALKYLATION;

D O I：

10.1021/ol403103u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：6250 / 6253

页数：4

共 50 条

[1] Synthesis of tri- and tetrasubstituted imidazoles
Paone, Daniel V.
Shaw, Anthony W.
TETRAHEDRON LETTERS, 2008, 49 (42) : 6155 - 6159
[2] Electrotelluration: A new approach to tri- and tetrasubstituted alkenes
Marino, JP
Nguyen, HN
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (18): : 6291 - 6296
[3] Stereoselective synthesis of tri- and tetrasubstituted olefins by tandem cyclization addition reactions featuring vinyl radicals
Gansäuer, A
Pierobon, M
Bluhm, H
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (17) : 3206 - +
[4] Synthesis of tri- and tetrasubstituted furans catalyzed by trifluoroacetic acid
Stauffer, F
Neier, R
ORGANIC LETTERS, 2000, 2 (23) : 3535 - 3537
[5] A general and stereoselective method for synthesis of tri- and tetrasubstituted alkenes
Maciagiewicz, I
Dybowski, P
Skowronska, A
TETRAHEDRON, 2003, 59 (32) : 6057 - 6066
[6] Organic and polymer chemistry of electrophilic tri- and tetrasubstituted ethylenes
Hall, HK
Padias, AB
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2004, 42 (12) : 2845 - 2858
[7] Enantioselective synthesis of di-, tri-, and tetrasubstituted allenylsilanes
Guintchin, BK
Bienz, S
ORGANOMETALLICS, 2004, 23 (21) : 4944 - 4951
[8] A new method for synthesis of tri- and tetrasubstituted alkenes.
Montgomery, J
Lozanov, M
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U170 - U170
[9] Synthesis of Tri- and Tetrasubstituted Alkenyl Boronates from Alkynes
Altarejos, Julia
Valero, Antonio
Manzano, Ruben
Carreras, Javier
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (30)
[10] Synthesis of functionalized tri- and tetrasubstituted vinylic tellurides from enolphosphates through vinylic substitution by lithium butyltellurolate
Barrientos-Astigarraga, RE
Castelani, P
Sumida, CY
Comasseto, JV
TETRAHEDRON LETTERS, 1999, 40 (44) : 7717 - 7720

← 1 2 3 4 5 →