Preparation of cyclic alkenylmagnesium reagents via an iodine/magnesium exchange

被引:62
作者
Ren, HJ [1 ]
Krasovskiy, A [1 ]
Knochel, P [1 ]
机构
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
关键词
D O I
10.1039/b415588b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of various cyclic alkenyl iodides with i-PrMgCl.LiCl produces the corresponding alkenylmagnesium reagents under mild conditions. After reaction with various electrophiles, like allylic halides, disulfides, aldehydes and acid chlorides, the expected products are obtained in 53-91% yield. Remarkably, the mild conditions of the I/Mg-exchange tolerate the presence of sensitive diene functionalities.
引用
收藏
页码:543 / 545
页数:3
相关论文
共 20 条
[1]   Stereoselective SN2-substitutions using polyfunctional lithium arylcuprates prepared by an exchange iodine-copper [J].
Calaza, MI ;
Yang, XY ;
Soorukram, D ;
Knochel, P .
ORGANIC LETTERS, 2004, 6 (04) :529-531
[2]   Highly anti-selective SN2′ substitutions of chiral cyclic 2-iodo-allylic alcohol derivatives with mixed zinc-copper reagents [J].
Calaza, MI ;
Hupe, E ;
Knochel, P .
ORGANIC LETTERS, 2003, 5 (07) :1059-1061
[3]  
Enders D, 2000, SYNLETT, P641
[4]   Selective halogen-magnesium exchange reaction via organomagnesium ate complex [J].
Inoue, A ;
Kitagawa, K ;
Shinokubo, H ;
Oshima, K .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4333-4339
[5]  
Kitagawa K, 2000, ANGEW CHEM INT EDIT, V39, P2481, DOI 10.1002/1521-3773(20000717)39:14<2481::AID-ANIE2481>3.0.CO
[6]  
2-J
[7]   Nucleophilic catalysis of the iodine-zinc exchange reaction: Preparation of highly functionalized diaryl zinc compounds [J].
Kneisel, FF ;
Dochnahl, M ;
Knochel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (08) :1017-1021
[8]  
Kneisel FF, 2002, SYNLETT, P1799
[9]   Highly functionalized organomagnesium reagents prepared through halogen-metal exchange [J].
Knochel, P ;
Dohle, W ;
Gommermann, N ;
Kneisel, FF ;
Kopp, F ;
Korn, T ;
Sapountzis, I ;
Vu, VA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (36) :4302-4320
[10]   SYNTHESIS AND REACTIVITY TOWARD ACYL CHLORIDES AND ENONES OF THE NEW HIGHLY FUNCTIONALIZED COPPER REAGENTS RCU(CN)ZNI [J].
KNOCHEL, P ;
YEH, MCP ;
BERK, SC ;
TALBERT, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2390-2392