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Palladium‐Catalyzed Stereospecific Substitution of α,β‐Unsaturated γ,δ‐Epoxy Esters by Alcohols with Double Inversion of Configuration: Synthesis of 4‐Alkoxy‐5‐hydroxy‐2‐pentenoates
Author(s) -
Yu XiaoQiang,
Yoshimura Fumihiko,
Ito Fumito,
Sasaki Minoru,
Hirai Atsushi,
Tanino Keiji,
Miyashita Masaaki
Publication year - 2008
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.200703889
Subject(s) - stereospecificity , palladium , stereoselectivity , catalysis , alkoxy group , epoxy , chemistry , substitution (logic) , walden inversion , substitution reaction , inversion (geology) , organic chemistry , alkyl , computer science , paleontology , structural basin , biology , programming language
Accessing the inaccessible : Highly functionalized compounds that were previously inaccessible can be readily prepared in a highly stereoselective manner, in high yields, and even in chiral forms by the palladium‐catalyzed substitution of α,β‐unsaturated γ,δ‐epoxy esters with various alcohols (see scheme). The products formed can serve as versatile synthetic intermediates for further transformations.