NEW SIGMATROPIC SEQUENCES BASED ON THE -WITTIG REARRANGEMENT OF THE BIS ALLYLIC ETHER SYSTEM A GENERAL APPROACH TO REGIOCONTROLLED C-C BOND FORMATION OF ALLYLIC MOIETIES LEADING TO UNSATURATED CARBONYL COMPOUNDS

Article abstract of DOI:10.1016/S0040-4020(01)90580-0

Four new sigmatropic sequences triggered by the regiocontrolled <2,3>-Wittig rearrangement of unsymmetrical bis-allylic ethers (1) to the 1,5-dien-3-ols (2) are described, which provide unique, regiocontrolled methods for the synthesis of a wide variety of unsaturated carbonyl compounds possessing interesting molecular frameworks.The newly developed sequences include the <2,3>-Wittig-Claisen, the tandem <2,3>-Wittig-oxy-Cope, the tandem oxy-Cope-Claisen, and the tandem oxy-Cope-Cope sequences.