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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.