Soluble polyisobutylene-supported reusable catalysts for olefin cyclopropanation

被引：23
作者：
Bergbreiter, David E. [1 ]
Tian, Jianhua [1 ]
机构：
[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 26期
基金：
美国国家科学基金会;
关键词：
cyclopropanation; bisoxazoline; polyisobutylene; polymer supports;
D O I：
10.1016/j.tetlet.2007.04.147
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Polyisobutylene oligomers (PIB) have been used as soluble supports for the immobilization of cyclopropanation catalysts. In addition to simple carboxylate ligands, chiral bisoxazolines have been successfully attached to these heptane-soluble polymers. Their use and recovery has been investigated using cyclopropanation of styrene as an example. An achiral PIB-bound Rh(II) catalyst showed good activity and could be easily recycled nine times using a liquid-liquid biphasic separation technique. PIB-supported bisoxazoline ligands for Cu(I) catalysts were also prepared. These chiral catalysts showed good catalytic activity and stereoselectivity. A chiral ligand prepared from phenylglycine provided the most effective stereocontrol and gave the trans- and cis-cyclopropanation products in 94% ee and 68% ee, respectively. All three PIB-bound chiral bisoxazoline-Cu(I) catalysts prepared could be reused five to six times. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4499 / 4503
页数：5
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