Copper-catalyzed [1,3]-alkoxy rearrangement for the selective synthesis of polycyclic ortho-aminoarenol derivatives
Literature Information
Publication Date
2021-09-18
DOI
10.1039/D1QO01189H
Impact Factor
5.281
Authors
Itaru Nakamura, Satoru Nozawa, Yasuhiro Ishida, Ichiro Muranushi, Alexandra Mayerweg, Masahiro Terada
View Original
Abstract
Copper-catalyzed [1,3]-alkoxy rearrangement reactions of polycyclic arenes, such as naphthalenes and phenanthrenes, proceeded efficiently to afford the corresponding ortho-aminoarenol derivatives in good to excellent yields with excellent ortho-selectivity. Through appropriate choice of an N-heterocyclic carbene (NHC) ligand, the reactions are applicable to not only a methoxy group but also readily deprotectable p-nitrobenzyloxy and methoxymethoxy groups. Moreover, the rearrangement of the N-methoxyamino group on the benzene ring of indoles proceeded efficiently, affording the corresponding functionalized indoles in a site-selective manner.
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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
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(3R,5R)-1-[(Benzyloxy)carbonyl]-5-methyl-3-piperidinecarboxylic acid
CAS Number:
1269757-29-0
Molecular Formula:
C15H19NO4
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