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ACS Omega · 2020 · IF 2.87

Electrosynthesis of Quinazolines and Quinazolinones via an Anodic Direct Oxidation C(sp3)-H Amination/C-N Cleavage of Tertiary Amine in Aqueous Medium

Zhenghong Zhou,Kangfei Hu,Jiawei Wang,Zhibin Li,Yan Zhang,Zhenggen Zha,Zhiyong Wang

An electrochemical synthesis for quinazolines and quinazolinones was developed via a C(sp3)-H amination/C-N cleavage by virtue of the anodic oxidation. The reaction can be carried out in aqueous media under mild conditions to afford the desired products with high yields. The reaction mechanism was proposed after detailed investigation.

研究领域: 有机化学 · 电化学

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Nature Catalysis · 2021 ·Vol. 4 ·期 5 ·364-373 · IF 41.813

Development of a versatile and efficient C–N lyase platform for asymmetric hydroamination via computational enzyme redesign

Cui Yinglu,Wang Yinghui,Tian Wenya,Bu Yifan,Li Tao,Cui Xuexian,Zhu Tong,Li Ruifeng,Wu Bian

Although C–N bonds are ubiquitous in natural products, pharmaceuticals and agrochemicals, biocatalysts forging these bonds with high atom-efficiency and enantioselectivity have been limited to a few select enzymes. In particular, ammonia lyases have emerged as powerful catalysts to access C–N bond formation via hydroamination. However, the use of ammonia lyases is rather restricted due to their narrow synthetic scope. Herein, we report the computational redesign of aspartase, a highly specific ammonia lyase, to yield C–N lyases with cross-compatibility of non-native nucleophiles and electrophiles. A wide range of non-canonical amino acids (ncAAs) are afforded with excellent conversion (up to 99%), regioselectivity >99% and enantioselectivity >99%. The process is scalable under industrially relevant protocols (exemplified in kilogram-scale synthesis) and can be facilely integrated in cascade reactions (demonstrated in the synthesis of β-lactams with N-1 and C-4 substitutions). This versatile and efficient C–N lyase platform supports the preparation of ncAAs and their derivatives, and will present opportunities in synthetic biology.

研究领域: 生物催化 · 酶工程 · 有机化学 · 合成生物学

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Electrosynthesis of Quinazolines and Quinazolinones via an Anodic Direct Oxidation C(sp3)-H Amination/C-N Cleavage of Tertiary Amine in Aqueous Medium

Development of a versatile and efficient C–N lyase platform for asymmetric hydroamination via computational enzyme redesign