Synthesis and reactivity of Z and E functionalized allylic fluorides

被引：8
|
作者：
Prakesch, M [1 ]
Grée, D [1 ]
Grée, R [1 ]
机构：
[1] ENSCR, Lab Synth & Activat Biomol, CNRS, UMR 6052, F-35700 Rennes, France
来源：
TETRAHEDRON | 2003年 / 59卷 / 44期
关键词：
fluorine; allylic fluoride; enone; enal;
D O I：
10.1016/j.tet.2003.08.068
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The allylic fluorides 1 and 2 are used as models to study the effect of the allylic C-F bond on the diastereoselectivity of reactions occurring on the vicinal double bond, as well as the compatibility of this C-F bond with various reagents. The configurational stability of the Z double bonds in enals and enones 1 and 3 is noteworthy. This allowed us to perform various types of reactions (including thermal Diels-Alder cycloadditions) on derivatives 1 with full control of the Z geometry. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8833 / 8841
页数：9
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