Tandem Cross-Dimerisation/Oxonia-Cope Reaction of Carbonyl Compounds to Homoallylic Esters and Lactones


  • We thank Dr. G. Brunner for NMR experiments, Dr. Z. Chen at Fudan University for X-ray measurements, and G. Tang at Fudan University for the high-resolution MS data.


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Conceptually different: This allyltransfer reaction is catalyzed by Lewis acids (LAs) and proceeds atom-economically by disproportionation of the carbonyl groups through organized oxonia-Cope transition states (see scheme). A stereoselective [n+4] ring enlargement leads to a variety of macrolides with 9- to 16-membered rings.