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Asymmetric Synthesis of 2′‐Trifluoromethylated Spiro‐pyrrolidine‐3,3′‐oxindoles via Squaramide‐Catalyzed Umpolung and 1,3‐Dipolar Cycloaddition
Author(s) -
Su Jinhuan,
Ma Zelin,
Li Xiaoyuan,
Lin Li,
Shen Zhiqiang,
Yang Peiju,
Li Yuan,
Wang Hailin,
Yan Wenjin,
Wang Kairong,
Wang Rui
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600688
Subject(s) - squaramide , chemistry , pyrrolidine , umpolung , cycloaddition , catalysis , organocatalysis , 1,3 dipolar cycloaddition , stereochemistry , stereocenter , medicinal chemistry , enantioselective synthesis , organic chemistry , combinatorial chemistry , nucleophile
The introduction of a trifluoromethyl group into the 2′‐position of spiro‐pyrrolidine‐3,3′‐oxindoles is described. By using 1 mol% of a quinine‐derived squaramide as catalyst, the 2,2,2‐trfluoroethylamine (CF 3 CH 2 NH 2 )‐derived ketimine is transformed initially into a trifluoromethylimine through an umpolung reaction. The subsequent 1,3‐dipolar cycloaddition gives the pharmaceutical important target compounds in excellent yields, enantioselectivities and diastereoselectivies.