4-Methyl-3-morpholinecarboxylic acid hydrochloride (1:1)
CAS Number:
1240518-90-4
Molecular Formula:
C6H12ClNO3
Decarboxylative Umpolung of conjugated enals to β-carbanions for intramolecular nucleophilic addition to an aldehyde
Literature Information
Publication Date
2017-05-09
DOI
10.1039/C6QO00846A
Impact Factor
5.281
Authors
Feng Liu, Jiaxin Tian, Yong Liu, Chuangan Tao, Hao Zhu, Aina Zhang, Dongfang Xu, Baoguo Zhao
View Original
Abstract
An interesting Umpolung strategy to generate β-carbanion equivalents from a conjugated enal has been developed. The enal group of compounds 7 was chemospecifically converted to a delocalized carbanion by decarboxylation of the in situ formed imine between the enal and 2,2-diphenylglycine (2), which then underwent nucleophilic addition at the β position of the enal to an intramolecular aldehyde group to give cyclized products 8 in 54–93% yields.
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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
cis-3-Amino-1-(trifluoromethyl)cyclobutanol hydrochloride (1:1)
CAS Number:
1408075-16-0
Molecular Formula:
C5H9ClF3NO
6-Bromo-3,4-dihydro-2H-1,4-benzoxazine hydrochloride (1:1)
CAS Number:
1260803-10-8
Molecular Formula:
C8H9BrClNO
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