phosphoryl}methyl 4-methylbenzenesulfonate structure](https://static.chemtradehub.com/structs/864/864068-45-1-ba7c.webp "{[3-(Hexadecyloxy)propoxy](hydroxy)phosphoryl}methyl 4-methylbenzenesulfonate structure")
{[3-(Hexadecyloxy)propoxy](hydroxy)phosphoryl}methyl 4-methylbenzenesulfonate
CAS Number:
864068-45-1
Molecular Formula:
C27H49O7PS
Brønsted acid-catalyzed dynamic kinetic resolution of in situ formed acyclic N,O-hemiaminals: cascade synthesis of chiral cyclic N,O-aminals
Literature Information
Publication Date
2021-09-16
DOI
10.1039/D1QO01135A
Impact Factor
5.281
Authors
Xue-Jiao Lv, Yong-Chao Ming, Hui-Chun Wu
View Original
Abstract
A Brønsted acid-catalyzed cascade acyclic N,O-hemiaminal formation/oxa-Michael reaction is developed for the synthesis of cis-2,6-disubstituted tetrahydropyrans bearing an exo amide group, that is, cyclic N,O-aminals. By using TsOH, various different amides including carboxyamides, carbamates, sulfonamides and even phosphoramides were applicable for the designed reaction sequence. By using chiral phosphoric acid, a wide range of enantioenriched cyclic N,O-aminal scaffolds were obtained. Detailed mechanistic investigations revealed that the good enantioselectivity can be attributed to a H2O controlled dynamic kinetic resolution of the in situ formed acyclic N,O-hemiaminal intermediate during the reaction process. Furthermore, a number of divergent transformations of the obtained products were investigated, leading to various synthetically useful heterocyclic architectures.
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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
![N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide structure](https://static.chemtradehub.com/structs/109/109032-22-6-7c88.webp "N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide structure")
N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide
CAS Number:
109032-22-6
Molecular Formula:
C13H12N2O6S
![[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-(2,2,2-trichloroethoxycarbonyloxy)propanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate structure](https://static.chemtradehub.com/structs/100/100431-55-8-7104.webp "[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-(2,2,2-trichloroethoxycarbonyloxy)propanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate structure")
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