Regio‐ and Stereocontrolled Introduction of Secondary Alkyl Groups to Electron‐Deficient Arenes through Copper‐Catalyzed Allylic Alkylation | Zendy

Makida Yusuke | Zendy; Ohmiya Hirohisa | Zendy; Sawamura Masaya | Zendy

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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.

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