Chiral phosphoric acid catalyzed enantioselective inverse-electron-demand oxa-Diels–Alder reactions to synthesize chiral tricyclic tetrahydropyran derivatives
Literature Information
Publication Date
2023-11-23
DOI
10.1039/D3QO01615C
Impact Factor
5.281
Authors
Fang Tian, Lin Peng, Liang-Liang Wang
View Original
Abstract
A series of enantioenriched tricyclic tetrahydropyran derivatives were achieved through chiral phosphoric acid catalyzed intramolecular inverse electron demand oxa-Diels–Alder (IEDODA) reactions, with good yields (up to 95%) and excellent stereocontrol (>20 : 1 dr, up to 99% ee). The achievement of such high enantioselectivity was ascribed to the rationally designed remote dual hydrogen bonding interaction, by which the conformation of the flexible substrate was well arranged by the catalyst in a reactive and stereoselective manner to participate in the transformation.
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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
![[3-(2,6-Dichlorophenyl)-5-isopropyl-1,2-oxazol-4-yl]methanol structure](https://static.chemtradehub.com/structs/278/278597-30-1-5c79.webp "[3-(2,6-Dichlorophenyl)-5-isopropyl-1,2-oxazol-4-yl]methanol structure")
[3-(2,6-Dichlorophenyl)-5-isopropyl-1,2-oxazol-4-yl]methanol
CAS Number:
278597-30-1
Molecular Formula:
C13H13Cl2NO2
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