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

Zhao MeiXin | Zendy; Zhu GuangYu | Zendy; Zhu HuiKai | Zendy; Zhao XiaoLi | Zendy; Ji Ming | Zendy; Shi Min | Zendy

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

Author(s) -

Zhao MeiXin,

Zhu GuangYu,

Zhu HuiKai,

Zhao XiaoLi,

Ji Ming,

Shi Min

Publication year - 2018

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201800511

Subject(s) - squaramide , cinchona , chemistry , cycloaddition , organocatalysis , alkaloid , enantioselective synthesis , cinchona alkaloids , stereoselectivity , organic chemistry , catalysis , stereochemistry

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.

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