无环（二烯）铁配合物和（二烯基）铁阳离子在有机合成中的最新应用
Recent Applications of Acyclic (Diene)iron Complexes and (Dienyl)iron Cations in Organic Synthesis.
作者信息
Donaldson William A, Chaudhury Subhabrata
机构信息
Department of Chemistry, Marquette University, P. O. Box 1881, Milwaukee, WI 53201-1881 USA.
出版信息
European J Org Chem. 2009 Aug;2009(23):3831-3843. doi: 10.1002/ejoc.200900141.
Abstract
Complexation of (tricarbonyl)iron to an acyclic diene serves to protect the ligand against oxidation, reduction and cycloaddition reactions while the steric bulk of this adjunct serves to direct the approach reagents to unsaturated groups attached to the diene onto the face opposite to iron. Furthermore, the Fe(CO)(3) moiety can serve to stabilize carbocation centers adjacent to the diene (i.e. pentadienyl-iron cations). Recent applications of these reactivities to the synthesis of polyene, cyclopropane, cycloheptadiene and cyclohexenone containing natural products or analogs will be presented.
摘要
（三羰基）铁与无环二烯的络合作用可保护配体免受氧化、还原和环加成反应的影响，同时该辅助基团的空间位阻可引导亲试剂与连接在二烯上的不饱和基团在与铁相对的面上发生反应。此外，Fe(CO)₃部分可用于稳定与二烯相邻的碳正离子中心（即戊二烯基铁阳离子）。本文将介绍这些反应性在合成含多烯、环丙烷、环庚二烯和环己烯酮的天然产物或类似物中的最新应用。
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J Org Chem. 2008 Sep 19;73(18):7236-45. doi: 10.1021/jo801446q. Epub 2008 Aug 20.
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