Ring‐Contraction Strategy for the Practical, Scalable, Catalytic Asymmetric Synthesis of Versatile γ‐Quaternary Acylcyclopentenes | Zendy

Hong Allen Y. | Zendy; Krout Michael R. | Zendy; Jensen Thomas | Zendy; Bennett Nathan B. | Zendy; Harned Andrew M. | Zendy; Stoltz Brian M. | Zendy

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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.

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