Journal
ORGANIC LETTERS
Volume 10, Issue 24, Pages 5613-5615Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol8022227
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Funding
- NSF [DMR-0094347]
- AFOSR
- MURI [FA9550-07-1-0534]
- NIH
- CCNE
- NCI [1U54 CA 119341-01]
- NSF Graduate Research Fellow
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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.
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