Chiral phosphoric acid-catalyzed asymmetric C(sp3)–H functionalization of biomass-derived 2,5-dimethylfuran via two sequential Cope-type rearrangements
Literature Information
Publication Date
2019-02-26
DOI
10.1039/C8QO01375F
Impact Factor
5.281
Authors
Lubin Xu, Haohua Chen, Jian Liu, Lan Zhou, Qing Liu
View Original
Abstract
Reported herein is the first organocatalytic asymmetric C(sp3)–H functionalization of biomass-derived 2,5-dimethylfuran with 3-hydroxy-3-indolyoxindoles to afford enantioenriched furan-derived 3,3′-disubstituted oxindoles in high enantioselectivity. This reaction is realized through chiral acid-catalyzed two sequential Cope-type rearrangements as proved by DFT calculations, which demonstrates a strategically new reactivity of 2,5-dimethylfuran, enabling the direct production of chiral chemicals from biomass-derived molecules.
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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
2-Methyl-2-propanyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate
CAS Number:
211429-79-7
Molecular Formula:
C15H17NO3
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