Temperature‐Dependent Cinchona Alkaloid Squaramide‐Catalyzed Asymmetric Formal [3+2] Cycloaddition of Isocyanoacetates with β‐Trifluoromethylated Enones

An efficient temperature‐dependent organocatalyzed asymmetric formal [3+2] cycloaddition reaction of α‐substituted isocyanoacetates to β‐trifluoromethylated enones by cinchona alkaloid‐derived squaramide has been investigated, affording the optically active trifluoromethylated 2‐pyrrolines in excell...

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Bibliographic Details
Published in:European journal of organic chemistry 2018-08, Vol.2018 (29), p.3997-4005
Main Authors: Zhao, Mei‐Xin, Zhu, Guang‐Yu, Zhu, Hui‐Kai, Zhao, Xiao‐Li, Ji, Ming, Shi, Min
Format: Article
Language:English
Subjects:
Cycloaddition
Enones
Isocyanoacetates
Optical activity
Organocatalysis
Pyrroles
Temperature dependence
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Summary:An efficient temperature‐dependent organocatalyzed asymmetric formal [3+2] cycloaddition reaction of α‐substituted isocyanoacetates to β‐trifluoromethylated enones by cinchona alkaloid‐derived squaramide has been investigated, affording the optically active trifluoromethylated 2‐pyrrolines in excellent yields (up to 98 %) and high stereoselectivities (>20:1 dr, up to >99 % ee) under mild conditions. A temperature‐dependent organocatalyzed asymmetric formal [3+2] cycloaddition reaction of isocyanoacetates to β‐trifluoromethylated enones is developed that directly affords chiral trifluoromethylated 2‐pyrrolines in good yield and high stereoselectivity.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201800511