立体选择性
化学
催化作用
基础(拓扑)
吡咯烷
加合物
选择性
甘氨酸
谷氨酸
加成反应
有机碱
核磁共振波谱
组合化学
氨基酸
有机化学
生物化学
数学分析
数学
作者
Parijat Borah,Yasuhiro Yamashita,Shū Kobayashi
标识
DOI:10.1002/anie.201701789
摘要
Abstract A novel methodology using CsF⋅Al 2 O 3 as a highly efficient, environmentally benign, and reusable solid‐base catalyst was developed to synthesize glutamic acid derivatives by stereoselective 1,4‐addition of glycine derivatives to α,β‐unsaturated esters. CsF⋅Al 2 O 3 showed not only great selectivity toward 1,4‐addtion reactions by suppressing the undesired formation of pyrrolidine derivations by [3+2] cycloadditions, but also offered high yields for the 1,4‐adduct with excellent anti diastereoselectivities. The catalyst was well characterized by using XRD, 19 F MAS‐NMR and 19 F NMR spectroscopy, FT‐IR, CO 2 ‐TPD, and XPS. And highly basic F from Cs 3 AlF 6 was identified as the most probable active basic site for the 1,4‐addition reactions. Continuous‐flow synthesis of 3‐methyl glutamic acid derivative was successfully demonstrated by using this solid‐base catalysis.
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