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Gold‐Catalyzed Synthesis of Quinolines from Propargyl Silyl Ethers and Anthranils through the Umpolung of a Gold Carbene Carbon
Author(s) -
Jin Hongming,
Tian Bin,
Song Xinlong,
Xie Jin,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201606043
Subject(s) - umpolung , propargyl , quinoline , carbene , silylation , chemistry , annulation , catalysis , aldol reaction , combinatorial chemistry , ring (chemistry) , organic chemistry , medicinal chemistry , nucleophile
A gold‐catalyzed cascade annulation of propargylic silyl ethers with anthranils proceeds through a sequential ring opening/1,2‐H‐shift/protodeauration/Mukaiyama aldol cyclization. This method offers a regiospecific and modular access to 2‐aminoquinolines and other quinoline derivatives under mild conditions and with a broad functional‐group tolerance. The conversion is possible on a gram scale, which underlines the synthetic practicability of this methodology. The versatility of the obtained scaffold has been demonstrated by useful postfunctionalization.