L-Pyroglutamic Sulphonamide as Hydrogen-Bonding Organocatalyst: Enantioselective Diels-Alder Cyclization to Construct Carbazolespirooxindoles
L-Pyroglutamic Sulphonamide as Hydrogen-Bonding Organocatalyst: Enantioselective Diels-Alder Cyclization to Construct Carbazolespirooxindoles
复制标题
L-焦谷氨酸磺酰胺作为氢键有机催化剂：对映选择性狄尔斯-阿尔德环化构建咔唑螺吲哚
DOI：
10.1021/acs.joc.7b00733
复制
发表时间：
2017
影响因子：
3.6
通讯作者：
Yang Hua
中科院分区：
文献类型：
--
作者：
Ren Ji Wei;Wang Jing;Xiao Jun An;Li Jun;Xiang Hao Yue;Chen Xiao Qing;Yang Hua
Hydrogen-bonding organocatalystsL-pyroglutamic sulphonamides were readily synthesized for the first time by fully exploiting the potentials ofL-pyroglutamic acid. The newly designed catalyst was successfully applied in catalyzing asymmetric Diels–Alder cyclization of methyleneindolinones with 2-vinyl-1H-indoles to efficiently assemble carbazolespirooxindoles in excellent stereoselectivity (up to 99% ee, >20:1 dr) and yields (up to 99%). Mechanistic studies disclosed that the well-designed hydrogen-bonding modes betweenL-pyroglutamic sulphonamide and substrates were crucial for stereocontrol in the cyclization.
