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Phosphine‐Catalyzed [3+2] Annulation of N ‐2,2,2‐Trifluoroethylisatin Ketimines with γ‐Substituted Allenoates: Synthesis of Spiro[indoline‐3,2′‐pyrrole]
Author(s) -
Wu XiaoYun,
Gao YuNing,
Shi Min
Publication year - 2019
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.201801794
Subject(s) - annulation , indoline , chemistry , phosphine , pyrrole , catalysis , moiety , combinatorial chemistry , medicinal chemistry , organocatalysis , organic chemistry , stereochemistry , enantioselective synthesis
Synthesis of spiro[indoline‐3,2′‐pyrrole] scaffold compounds from N ‐2,2,2‐trifluoroethylisatin ketimines and γ‐substituted allenoates through a phosphine‐catalyzed [3+2] annulation process has been developed, which could afford an unprecedented access to spirocyclic oxindoles with functionalized CF 3 moiety containing five‐membered rings. The new synthetic protocol used readily available N ‐2,2,2‐trifluoroethylisatin ketimines as the starting materials, inexpensive PPh 3 as the catalyst, and the corresponding products were obtained with yields up to 85 % under mild conditions.