follow us login

aza-cope重排(氮杂科甫重排)指在重排分子中含亚胺离子结构单元的氮杂-[3,3]-σ迁移重排,生成产物为胺的衍生物。


image.png


反应机理


氮杂科甫重排的起因是mannich反应,先形成亚胺离子继而引发科甫重排。一般而言,氧杂及氮杂科甫重排比纯碳链的科甫重排温度要低,反应要快。


image.png


反应实例


image.png


image.png


image.png


参考文献


1. oehlschlager, a. c., zalkow, l. h. bridged ring compounds. x. j. org. chem. 1965, 30, 4205-4211.

2. hill, r. k., gilman, n. w. tetrahedron lett. 1967, 1421-1423.

3. lipkowitz, k. b., scarpone, s., mccullough, d., barney, c. tetrahedron lett. 1979, 2241-2244.

4. brummond, k. m., lu, j. org. lett. 2001, 3, 1347-1349.

5. bennett, d. j., hamilton, n. m. tetrahedron lett. 2000, 41, 7961-7964.

6. madin, a., o'donnell, c. j., oh, t., old, d. w., overman, l. e., sharpe, m. j. angew. chem., int. ed. engl. 1999, 38, 2934-2936.

7. knight, s. d., overman, l. e., pairaudeau, g. j. am. chem. soc. 1995, 117, 5776-5788.


摘自:有机人名反应——机理及应用 第四版,strategic applications of named reactions in organic synthesis


contact us

feel free to call us on
025-85998075

our email

drop us a line anytime at
,
and we’ll get back soon.

our address

come visit us at 2 qiande road, life science high tech zone, jiang ning district, nanjing, jiangsu province, china

网站地图