![2,2'-{2,2-Propanediylbis[(2,6-dibromo-4,1-phenylene)oxy]}diethanol structure](https://static.chemtradehub.com/structs/416/4162-45-2-b3d6.webp "2,2'-{2,2-Propanediylbis[(2,6-dibromo-4,1-phenylene)oxy]}diethanol structure")
2,2'-{2,2-Propanediylbis[(2,6-dibromo-4,1-phenylene)oxy]}diethanol
CAS Number:
4162-45-2
Molecular Formula:
C19H20Br4O4
Organocatalytic asymmetric [4 + 1] annulation of in situ generated ortho-quinomethanes with 4-halo pyrazolones: straightforward access to chiral spiro-benzofuran pyrazolones
Literature Information
Publication Date
2019-04-17
DOI
10.1039/C9QO00332K
Impact Factor
5.281
Authors
Ming-Ming Chu, Suo-Suo Qi, Yi-Feng Wang, Biao Wang, Zhen-Hui Jiang, Dan-Qian Xu, Zhen-Yuan Xu
View Original
Abstract
A highly straightforward route to enantiomerically enriched spiro-benzofuran pyrazolones has been achieved via chiral amine squaramide catalyzed [4 + 1] annulation of in situ generated ortho-quinomethanes with the novel C1 synthons of 4-halo pyrazolones. In oil–water biphases, high yields (up to 95%) and high to excellent stereoselectivities (up to 99 : 1 dr, 99% ee) of the resulting 4-spiropyrazolones with a wide substrate scope could be achieved. Furthermore, the present protocol provided an arbitrary access to all four possible stereoisomers of the spiro-benzofuran pyrazolones via an appropriate choice of C1 synthons and chiral catalysts.
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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
Oxalic acid compound with cyclohexylsulfamothioic O-acid (11)
CAS Number:
31895-22-4
Molecular Formula:
C7H13NO4S3
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