A mild and efficient method for the synthesis of a new optically active diallyl selenide and its catalytic activity in the allylic chlorination of natural terpenes

被引：15

作者：

Boualy, Brahim ^{[1
]}

El Houssame, Soufiane ^{[1
]}

Sancineto, Luca ^{[2
]}

Santi, Claudio ^{[2
]}

Ali, Mustapha Ait ^{[3
]}

Stoeckli-Evans, Helen ^{[4
]}

El Firdoussi, Larbi ^{[3
]}

机构：

[1] Univ Hassan 1er, Fac Polydisciplinaire Khouribga, Lab Chim & Modelisat Math, BP 145, Khouribga 25000, Morocco

[2] Univ Perugia, Dept Pharmaceut Sci, Grp Catalysis & Organ Green Chem, Via Liceo 1, I-06100 Perugia, Italy

[3] Univ Cadi Ayyad, Fac Sci Semlalia, Dept Chim, Equipe Chim Coordinat & Catalyse, BP 2390, Marrakech 40001, Morocco

[4] Univ Neuchatel, Inst Phys, CH-2000 Neuchatel, Switzerland

来源：

NEW JOURNAL OF CHEMISTRY | 2016年 / 40卷 / 04期

关键词：

UNSYMMETRICAL DIORGANYL SELENIDES; DIPHENYL DISELENIDES; CHEMISTRY; CLEAVAGE; COMPLEXES; CHLORIDES; OLEFINS;

D O I：

10.1039/c5nj02797g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A mild and convenient method for the synthesis of a new optically active bis(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)selenide 1 from the corresponding bicyclic terpene is described. The structure of the obtained organoselenium compound was established using H-1, C-13, Se-77-NMR spectroscopy and X-ray diffraction studies. Its application as a catalyst in the allylic chlorination of terpenic olefins has been successfully investigated under mild conditions. The reaction showed high selectivity affording the corresponding chlorides in good to excellent yields. The use of enantiomerically pure monoterpenes as starting materials allowed the preparation of asymmetric allyl chlorides through a process controlled by the substrate.

引用

页码：3395 / 3399

页数：5