A domino reaction for the synthesis of 2-amino-4 H -chromene derivatives using bovine serum albumin as a catalyst

Li, Lingyu; Zeng, Qing-Qing; Yang, Yaxuan; Hu, Hong-Feng; Xu, Man; Guan, Zhi; He, Yan‐Hong

doi:10.1016/j.molcatb.2015.08.005

Cited by 18 publications

(2 citation statements)

References 37 publications

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“…BSA could also catalyze the synthesis of 2-amino-4H-chromene derivatives from 2-hydroxychalcones. [16] However, these methods focused on the synthesis of benzofuran and benzopyran derivatives with little attention on their stereooutcome. The synthesis of other complex chiral oxygencontaining benzo-fused heterocycles through biocatalysis, such as benzoxepine skeleton in natural product leptosphaerin D, has not been developed due to the strict reactions and substrate specificity of elucidated natural enzymes.…”

Section: Introductionmentioning

confidence: 99%

Photoenzymatic Enantioselective Synthesis of Oxygen‐Containing Benzo‐Fused Heterocycles

Zhu,

Yuan,

Deng

et al. 2023

Angew Chem Int Ed

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New‐to‐nature biocatalysis in organic synthesis has recently emerged as a green and powerful strategy for the preparation of valuable chiral products, among which chiral oxygen‐containing benzo‐fused heterocycles are important structural motifs in pharmaceutical industry. However, the asymmetric synthesis of these compounds through radical‐mediated methods is challenging. Herein, a novel asymmetric radical‐mediated photoenzymatic synthesis strategy is developed to realize the efficient enantioselective synthesis of oxygen‐containing benzo‐fused heterocycles through structure‐guided engineering of a flavin‐dependent ‘ene’‐reductase GluER. It shows that variant GluER‐W100H could efficiently produce various benzoxepinones, chromanone and indanone with different benzo‐fused rings in high yields with great stereoselectivities under visible light. Moreover, these results are well supported by mechanistic experiments, revealing that this photoenzymatic process involves electron donor‐acceptor complex formation, single electron transfer and hydrogen atom transfer. Therefore, we provide an alternative green approach for efficient chemoenzymatic synthesis of important chiral skeletons of bioactive pharmaceuticals.

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Section: Introductionmentioning

confidence: 99%

Photoenzymatic Enantioselective Synthesis of Oxygen‐Containing Benzo‐Fused Heterocycles

Zhu,

Yuan,

Deng

et al. 2023

Angew Chem Int Ed

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“…In some cases, the 4Hchromene ring is closed in one-pot and solvent-free synthesis using grindstone chemistry [34] (by simple grinding). Bovine serum albumin is also used as a catalyst in a domino reaction for the synthesis of 2-amino-4H-chromene derivatives [35]. 2,2,2-trifluoroethanol is used, too, as a metal-free and reusable medium in a facile and efficient synthesis of 2-amino-3-cyano-4H-chromenes and tetrahydrobenzo[b]pyrans [36].…”

Section: Introductionmentioning

confidence: 99%

Study on the Synthesis of Some (Un)Substituted 2-Amino-4-aryl-7-hydroxy-4H-chromene-3-carbonitriles in the Water Medium

Thành

Hai

Hien

et al. 2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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Advancements in the Preparation of 4H‐Chromenes: An Overview

et al. 2023

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Functionalized 4H‐chromenes represent one class of the most important structural scaffolds in both synthetic and medicinal chemistry. They often appear in an arrange of biological natural products, pharmaceutical agents and drug candidates. The significance has stimulated the development of efficient methodologies for the synthesis of such compounds. In this review, a comprehensive discussion on different synthetic approaches to 4H‐chromenes has been presented with an emphasis on reaction features and mechanisms. Three main categories are outlined: 1) nucleophilic addition to 2H‐chromene derivatives, 2) 4H‐chromene ring formation involved cycloaddition or cyclization reactions, and 3) miscellaneous reactions.

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A domino reaction for the synthesis of 2-amino-4 H -chromene derivatives using bovine serum albumin as a catalyst

Cited by 18 publications

References 37 publications

Photoenzymatic Enantioselective Synthesis of Oxygen‐Containing Benzo‐Fused Heterocycles

Photoenzymatic Enantioselective Synthesis of Oxygen‐Containing Benzo‐Fused Heterocycles

Study on the Synthesis of Some (Un)Substituted 2-Amino-4-aryl-7-hydroxy-4H-chromene-3-carbonitriles in the Water Medium

Advancements in the Preparation of 4H‐Chromenes: An Overview

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