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A New Class of Substrates for Nucleophilic 5‐ endo ‐trig Cyclization, 2‐Trifluoromethyl‐1‐alkenes: Synthesis of Five‐Membered Hetero‐ and Carbocycles That Bear Fluorinated One‐Carbon Units
Author(s) -
Ichikawa Junji,
Iwai Yu,
Nadano Ryo,
Mori Takashi,
Ikeda Masahiro
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200700324
Subject(s) - trifluoromethyl , nucleophile , chemistry , carbon fibers , class (philosophy) , medicinal chemistry , organic chemistry , stereochemistry , mathematics , philosophy , alkyl , catalysis , epistemology , algorithm , composite number
Disfavored 5‐ endo ‐trig cyclizations were achieved in 2‐trifluoromethyl‐1‐alkenes with a nucleophilic nitrogen, oxygen, sulfur, or carbon atom through 1) intramolecular S N 2′ reaction with loss of a fluoride ion or 2) intramolecular nucleophilic addition to the vinylic group. This reaction manifold provides a versatile method for the synthesis of indolines, indoles, pyrrolidines, tetrahydrofurans, 2,3‐dihydrobenzo[ b ]thiophenes, tetrahydrothiophenes, and cyclopentanes that bear a fluorinated one‐carbon unit such as a difluoromethylene, difluoromethyl, or trifluoromethyl group.