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Synthesis of δ-Lactones via Aldol, Cyclo-propanation, and Ring-Opening Cascade
J. Peed, I. Periñán Domínguez, I. R. Davies, M. Cheeseman, J. E. Taylor, G. Kociok-Köhn, S. D. Bull*
University of Bath, UK
19 August 2011 (online)
The authors describe a reaction sequence to access highly enantiomerically enriched δ-lactones. Using this reaction sequence, products containing up to four contiguous stereocenters could be formed. The reported sequence utilized the Evans auxiliary as a source of chirality in an aldol reaction. Subsequent stereocenters are generated through diastereoselective cyclopropanation and mercury-promoted cyclopropane ring opening.