[2,3]-wittig rearrangement initiated by 1,5-hydrogen atom transfer from an o-iodophenyl group on the α-carbon of allylic ethers by reduction with SmI2

被引：6
|
作者：
Kunishima, M [1 ]
Hioki, K [1 ]
Nakata, D [1 ]
Nogawa, S [1 ]
Tani, S [1 ]
机构：
[1] Kobe Gakuin Univ, Fac Pharmaceut Sci, Nishi Ku, Kobe, Hyogo 6512180, Japan
来源：
CHEMISTRY LETTERS | 1999年 / 07期
关键词：
D O I：
10.1246/cl.1999.683
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Intramolecular 1,5-hydrogen atom transfer of an aryl radical generated by reduction of an o-iodophenyl group on the allylic position of allyl ethers by SmI2 regioselectively generates alpha-allyloxy carbanions, which undergo [2,3]-Wittig rearrangement to afford a substituted 4-phenyl-3-buten-1-ol. The effect of HMPA concentration on distribution of the 1,5-hydrogen transfer giving Wittig rearranged products and hydrogen abstraction giving reductive deiodination products is described.
引用
收藏
页码：683 / 684
页数：2
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