SN2' SELECTIVE ALKYLATION OF ALLYLIC CHLORIDES AND MESYLATES WITH RZNX REAGENTS GENERATED FROM GRIGNARD-REAGENTS, ZINC-CHLORIDE, LITHIUM-CHLORIDE, AND CU(II)-SALTS

被引:29
作者
FUJII, N
NAKAI, K
HABASHITA, H
YOSHIZAWA, H
IBUKA, T
GARRIDO, F
MANN, A
CHOUNAN, Y
YAMAMOTO, Y
机构
[1] CTR NEUROCHIM,PHARMACOCHIM MOLEC LAB,CNRS,F-67084 STRASBOURG,FRANCE
[2] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN
关键词
D O I
10.1016/S0040-4039(00)60534-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of RMgX (1 equiv. R = alkyl; X = Cl, Br) with ZnCl2 (1 equiv.) in a mixed solvent of THF and Et2O leads to a highly turbid white suspension. Addition of LiCl (1 approximately 2 equiv.) solubilizes the insoluble species to yield a colorless clear solution. Addition of a catalytic amount of a Cu(II)-salt followed by allylic halides or mesylates at 0-degrees-C approximately room temperature yielded S(N)2' products in high yields. Application for the synthesis of (E)-alkene dipeptide isosteres is also reported.
引用
收藏
页码:4227 / 4230
页数:4
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