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

EB Pentzer, T Gadzikwa, SBT Nguyen

Index: Pentzer, Emily B.; Gadzikwa, Tendai; Nguyen, Sonbinh T. Organic Letters, 2008 , vol. 10, # 24 p. 5613 - 5615

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Citation Number: 20

Abstract

A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the α, ω-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 ...