Palladium‐Catalyzed Asymmetric Allylic Alkylation of Cyclic Dienol Carbonates: Efficient Route to Enantioenriched γ‐Butenolides Bearing an All‐Carbon α‐Quaternary Stereogenic Center | Zendy

Fournier Jeremy | Zendy; Lozano Oscar | Zendy; Menozzi Candice | Zendy; Arseniyadis Stellios | Zendy; Cossy Janine | Zendy

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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.

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