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Copper‐Catalyzed γ‐Selective and Stereospecific Direct Allylic Alkylation of Terminal Alkynes: Synthesis of Skipped Enynes
Author(s) -
Makida Yusuke,
Takayama Yurie,
Ohmiya Hirohisa,
Sawamura Masaya
Publication year - 2013
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.201300785
Subject(s) - allylic rearrangement , stereospecificity , stereoselectivity , chemistry , regioselectivity , tsuji–trost reaction , terminal (telecommunication) , stereochemistry , combinatorial chemistry , catalysis , computer science , organic chemistry , computer network
Skipping out : The title reaction using internal secondary allylic phosphates proceeded with excellent γ regioselectivity and E stereoselectivity to give skipped enynes. Enantioenriched secondary allylic phosphates proceeded with 1,3‐ anti stereochemistry to afford the corresponding chiral 1,4‐enynes, which were used for various derivatizations and the formal total synthesis of a GnRH antagonist. phen=1,10‐phenanthroline.