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N-Primary-amine tetrapeptide-catalyzed highly asymmetric Michael addition of aliphatic aldehydes to maleimides.
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2020-08-20 , DOI: 10.1039/d0ob01457e
Zhi-Hong Du 1 , Wen-Juan Qin , Bao-Xiu Tao , Meng Yuan , Chao-Shan Da
Affiliation  

The highly asymmetric Michael addition reaction between maleimides and aliphatic aldehydes catalyzed by low-loading β-turn tetrapeptides with excellent yields and enantioselectivities at room temperature was reported. α-Branched and α-unbranched aldehydes both are suitable nucleophiles. N-Aryl, alkyl and hydrogen maleimides all are well tolerated and led to high yields and enantioselectivities. The transformation can be enlarged to the gram scale without decrease in the yield and enantioselectivity. Furthermore, the succinimides were converted into γ-lactams and γ-lactones, showing good practicality of this work. Some reaction intermediates in the proposed reaction mechanism can be captured with the HR-MS method.

中文翻译:

N-伯胺四肽催化脂肪醛与马来酰亚胺的高度不对称迈克尔加成。

报道了由低负载β-转角四肽催化的马来酰亚胺和脂肪醛之间的高度不对称迈克尔加成反应,在室温下具有优异的收率和对映选择性。α-支链和 α-非支链醛都是合适的亲核试剂。N-芳基、烷基和氢马来酰亚胺均具有良好的耐受性并导致高产率和对映选择性。转化可以扩大到克级而不降低产率和对映选择性。此外,将琥珀酰亚胺转化为γ-内酰胺和γ-内酯,显示了这项工作的良好实用性。所提出的反应机制中的一些反应中间体可以用 HR-MS 方法捕获。
更新日期:2020-09-16
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