Catalytic asymmetric substitution of ortho-hydroxybenzyl alcohols with tetronic acid-derived enamines: enantioselective synthesis of tetronic acid-derived diarylmethanes
Literature Information
Publication Date
2016-12-12
DOI
10.1039/C6QO00549G
Impact Factor
5.281
Authors
Meng-Meng Xu, Hai-Qing Wang, Ying Wan, Guofeng He, Jingjing Yan, Shu Zhang, Shu-Liang Wang, Feng Shi
View Original
Abstract
The first catalytic asymmetric substitution of ortho-hydroxybenzyl alcohols with enamines has been established, which afforded tetronic acid-derived diarylmethanes in considerable yields and good enantioselectivities (up to 89% yield, 98 : 2 er). This reaction not only provided an efficient method for enantioselective synthesis of tetronic acid-derived diarylmethanes with biological relevance, but also fulfilled the task of developing catalytic asymmetric substitution of ortho-hydroxybenzyl alcohols by using tetronic acid-derived enamines as competent nucleophiles. More importantly, the preliminary biological evaluation of some selected products revealed that this class of chiral tetronic acid-derived diarylmethanes exhibited strong cytotoxicity to HT-29, MCF-7 and TE-13 cancer cell lines.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![Methyl 3-({2'-[(E)-(hydroxyhydrazono)methyl]-4-biphenylyl}methyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate structure](https://static.chemtradehub.com/structs/149/1499167-72-4-034a.webp "Methyl 3-({2'-[(E)-(hydroxyhydrazono)methyl]-4-biphenylyl}methyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate structure")
Methyl 3-({2'-[(E)-(hydroxyhydrazono)methyl]-4-biphenylyl}methyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate
CAS Number:
1499167-72-4
Molecular Formula:
C23H20N4O4
(S)-3-((tert-Butoxycarbonyl)amino)-4-(4-(tert-butyl)phenyl)butanoic acid
CAS Number:
403661-85-8
Molecular Formula:
C19H29NO4
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