Synthesis of planar chiral ferrocenyl sulfides and evaluation as catalysts for the asymmetric epoxidation of aldehydes

被引:7
作者
Minière, S [1 ]
Reboul, V [1 ]
Metzner, P [1 ]
机构
[1] ENSICAEN Univ, CNRS, UMR 6507, Lab Chim Mol & Thioorgan, 6 Blvd Marechal Juin, F-14050 Caen, France
关键词
ferrocenes; planar chirality; sulfides; sulfur ylides; epoxidation; oxiranes;
D O I
10.3998/ark.5550190.0006.b14
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New ferrocenyl sulfides, exhibiting planar chirality, have been prepared. They incorporate various heteroatom groups, and in some cases central chirality ( sulfur or carbon). They were evaluated as catalysts for the asymmetric epoxidation of aldehydes via sulfonium ylides. A one-pot reaction has been achieved, involving addition of benzaldehyde, benzyl bromide, 20% molar equivalent of the ferrocenyl sulfide, sodium iodide in a mixture of tert-butanol and water. Good yields of stilbene oxide were obtained, with enantiomeric excesses up to 53%.
引用
收藏
页码:161 / 177
页数:17
相关论文
共 46 条