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Regio‐ and Stereocontrolled Introduction of Secondary Alkyl Groups to Electron‐Deficient Arenes through Copper‐Catalyzed Allylic Alkylation
Author(s) -
Makida Yusuke,
Ohmiya Hirohisa,
Sawamura Masaya
Publication year - 2012
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.201200809
Subject(s) - allylic rearrangement , stereocenter , tsuji–trost reaction , chemistry , stereoselectivity , alkyl , alkylation , copper , catalysis , medicinal chemistry , pyridine , organic chemistry , enantioselective synthesis
Copper‐catalyzed allylic alkylation of azoles, a pyridine N ‐oxide, and fluoroarenes with secondary allylic phosphates proceeded under mild reaction conditions with excellent γ‐ E ‐selectivity. The reactions with enantioenriched allylic phosphates proceeded with 1,3‐ anti stereoselectivity to generate an allylic stereogenic center at the position α to the aromatic ring.