一种有机催化多米诺迈克尔-烷基化反应：螺环戊酮吲哚酮和特窗酸支架的高对映选择性构建
An organocatalytic domino Michael-alkylation reaction: highly enantioselective construction of spiro-cyclopentanoneoxindoles and tetronic acid scaffolds.
作者信息
Zhou Jing, Wang Qi-Lin, Peng Lin, Tian Fang, Xu Xiao-Ying, Wang Li-Xin
机构信息
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
出版信息
Chem Commun (Camb). 2014 Dec 4;50(93):14601-4. doi: 10.1039/c4cc05207b.
A new organocatalytic asymmetric domino Michael-alkylation reaction of methyleneindolinones and γ-halogenated-β-ketoesters is described. A variety of spiro-cyclopentanoneoxindoles were obtained in high yields (up to 96%), good diastereoselectivities (up to 12 : 1 dr) and excellent enantioselectivities (up to >99% ee) via α-alkylation. Interestingly, O-alkylated products with tetronic acid motifs could be obtained by tuning the N-protecting groups on methyleneindolinones with excellent enantioselectivities (up to >99% ee).
本文描述了一种新型的亚甲基吲哚酮与γ-卤代-β-酮酯的有机催化不对称多米诺迈克尔-烷基化反应。通过α-烷基化反应，以高产率（高达96%）、良好的非对映选择性（高达12:1 dr）和优异的对映选择性（高达>99% ee）得到了多种螺环戊酮氧化吲哚。有趣的是，通过调节亚甲基吲哚酮上的N-保护基，可以得到具有特窗酸基序的O-烷基化产物，且对映选择性优异（高达>99% ee）。
Zotero 插件