Highly regio-, diastereo- and enantioselective deracemization of axially chiral 3-alkylideneoxindoles
Highly regio-, diastereo- and enantioselective deracemization of axially chiral 3-alkylideneoxindoles
复制标题
轴向手性 3-亚烷基氧吲哚的高度区域选择性、非对映选择性和对映选择性去消旋作用
DOI：
10.1039/c7cc05164f
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发表时间：
2017
影响因子：
4.9
通讯作者：
Feng Xiaoming
中科院分区：
文献类型：
--
作者：
Mei Hongjiang;Lin Lili;Wang Lifeng;Dai Li;Liu Xiaohua;Feng Xiaoming
利用手性N，N′-二氧化物/Sc（III）配合物催化体系，首次实现了未保护的外消旋3-（4-烷基环己叉基）吲哚啉-2-酮与查尔酮的一步直接乙烯基Michael反应的催化不对称动态拆分.合成了一系列在α-、γ-和δ′-位上具有三个立体中心的（Z）-4-烷基-2-（（3-氧代-1，3-二芳基丙基）环己叉基）-吲哚啉-2-酮，产率高达95%，ee为98%，dr为99/1。
The first catalytic asymmetric dynamic resolution of unprotected racemic 3-(4-alkylcyclohexylidene)indolin-2-ones via a one-step direct vinylogous Michael reaction with chalcones was realized using a chiral N,N′-dioxide/Sc(III) complex catalytic system. A variety of (Z)-4-alkyl-2-((3-oxo-1,3-diarylpropyl)cyclohexylidene)-indolin-2-ones with three stereogenic centers at ξ-, γ- and δ′-positions were obtained in up to 95% yield, 98% ee and 99/1 dr. A possible transition state was proposed to explain the origin of the stereoselectivity.