The Vinylogous Intramolecular Morita−Baylis−Hillman Reaction: Synthesis of Functionalized Cyclopentenes and Cyclohexenes with Trialkylphosphines as Nucleophilic Catalysts

2002/02/26 by Scott A. Frank, Dustin J. Mergott, William Roush · 5 citations
Chemistry · Biochemistry, Genetics and Molecular Biology · #Asymmetric Synthesis and Catalysis #Synthetic Organic Chemistry Methods #Synthesis and Biological Activity

paper · doi:10.1021/ja017123j

openalex publication_date 2002/02/26 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26

Abstract

The development of the vinylogous intramolecular Morita-Baylis-Hillman reaction for the synthesis of functionalized cyclopentenes and cyclohexenes is described. The reaction involves the trialkyphosphine-catalyzed cyclization of 1,6- or 1,7-diactivated 1,5-hexadienes or 1,6-heptadienes, containing carboxyaldehyde, methyl ketone, or methoxycarbonyl as the olefin activating groups. A representative example of this reaction is the Me(3)P-catalyzed cyclization of 1a in tert-amyl alcohol, which provides the substituted cyclopentene 2a in 95% yield and with 97:3 regioselectivity.

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