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Palladium‐Catalyzed Asymmetric Allylic Alkylation of Cyclic Dienol Carbonates: Efficient Route to Enantioenriched γ‐Butenolides Bearing an All‐Carbon α‐Quaternary Stereogenic Center
Author(s) -
Fournier Jeremy,
Lozano Oscar,
Menozzi Candice,
Arseniyadis Stellios,
Cossy Janine
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.201206368
Subject(s) - stereocenter , tsuji–trost reaction , quaternary carbon , allylic rearrangement , palladium , catalysis , chemistry , quaternary , enantioselective synthesis , organic chemistry , biology , paleontology
Alpha, beta, gamma : Allyl dienol carbonates ( 1 ) served as substrates for the title reaction to afford the furanones 2 in both high yields and high enantioselectivities. These furanones were eventually converted into valuable building blocks including γ‐tertiary and γ‐quaternary furanones ( 3 ) as well as β‐quaternary butyrolactones ( 4 ). This method was used as a key step in the total synthesis of (−)‐nephrosteranic acid and (−)‐roccellaric acid.