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Copper‐Catalyzed Asymmetric Synthesis of Borylated cis ‐Disubstituted Indolines
Author(s) -
Li DingXi,
Kim Jiwon,
Yang Jung Woon,
Yun Jaesook
Publication year - 2018
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.201800121
Subject(s) - chemistry , moiety , intramolecular force , nucleophile , alkene , imine , diastereomer , catalysis , hydroamination , copper , medicinal chemistry , stereochemistry , organic chemistry
A copper‐catalyzed, intramolecular borylative cyclization of vinyl arenes with imines is reported, which affords enantio‐enriched indolines as a single diastereomer under mild conditions. A benzylcopper species is generated by Cu‐Bpin addition to the alkene, which then acts as a nucleophile for intramolecular imine addition. The reaction is applicable to various vinyl arenes with an imine moiety at the ortho ‐position, including heterocycles, for formation of borylated indolines in good yields and ee values up to 90 %.