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Ring‐Contraction Strategy for the Practical, Scalable, Catalytic Asymmetric Synthesis of Versatile γ‐Quaternary Acylcyclopentenes
Author(s) -
Hong Allen Y.,
Krout Michael R.,
Jensen Thomas,
Bennett Nathan B.,
Harned Andrew M.,
Stoltz Brian M.
Publication year - 2011
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.201007814
Subject(s) - enantioselective synthesis , computer science , quaternary carbon , scalability , catalysis , combinatorial chemistry , chemistry , schematic , exploit , organic chemistry , database , engineering , computer security , electronic engineering
Contraction action! A simple protocol for the catalytic asymmetric synthesis of highly functionalized γ‐quaternary acylcyclopentenes (see schematic) in up to 91 % overall yield and 92 % ee has been developed. The reaction sequence employs a palladium‐catalyzed enantioselective alkylation reaction and exploits the unusual stability of β‐hydroxy cycloheptanones to achieve a general and robust method for performing two‐carbon ring contractions.