Ring-opening reactions of MCPs with sulfonamides promoted by metal triflate Lewis acids

被引:45
|
作者
Chen, Y [1 ]
Shi, M [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 02期
关键词
D O I
10.1021/jo035233y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of aromatic MCPs with sulfonamides catalyzed by Lewis acids affords the corresponding ring-opened homoallylic sulfonamides in good yields and the reaction of aliphatic MCPs with sulfonamides gives the corresponding pyrrolidine derivatives under the same conditions. Through deuterium-labeling experiments, we found that the reaction process is involved with the rearrangement of a cyclopropylcarbinyl cation and a nonclassic carbonium ion.
引用
收藏
页码:426 / 431
页数:6
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