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

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

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

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.
Original languageEnglish (US)
Pages (from-to)2808-2812
Number of pages5
JournalAngewandte Chemie
Volume123
Issue number12
DOIs
StatePublished - Feb 24 2011
Externally publishedYes

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