Organocatalytic asymmetric synthesis of highly functionalized spiro-thiazolone–cyclopropane-oxindoles bearing two vicinal spiro quaternary centers
Literature Information
Publication Date
2019-03-14
DOI
10.1039/C9QO00145J
Impact Factor
5.281
Authors
Shengzheng Wang, Zhongjie Guo, Ying Wu, Wei Liu, Xueying Liu, Shengyong Zhang, Chunquan Sheng
View Original
Abstract
An effective organocatalytic asymmetric Michael/alkylation cascade reaction of 5-alkenyl thiazolones with 3-chloroxindoles catalyzed by Takemoto's bifunctional aminothiourea catalyst was developed. A variety of highly functionalized spiro-thiazolone–cyclopropane-oxindoles with three contiguous stereocenters, including two vicinal quaternary centers, were obtained in good yields (60%–86%) with moderate to good diastereoselectivities (up to 9.4 : 1 dr) and good enantioselectivities (up to 93% ee).
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
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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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