Substrate Encapsulation: An Efficient Strategy for the RCM Synthesis of Unsaturated ϵ-Lactones

2008/11/17 by Emily Pentzer, Tendai Gadzikwa, SonBinh T. Nguyen · 2 citations
Chemistry · Biochemistry, Genetics and Molecular Biology · #Synthetic Organic Chemistry Methods #Chemical Synthesis and Analysis #Advanced Synthetic Organic Chemistry

paper · doi:10.1021/ol8022227

openalex publication_date 2008/11/17 · openalex created_date 2016/06/24 · openalex updated_date 2026/08/01

Abstract

A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.

Cited by

• Equilibrium Ring-Closing Metathesis
• Ring-closing metathesis [wikipedia]

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