CHIRALITY TRANSMISSION VIA TANDEM SIGMATROPIC REARRANGEMENT: REGIO- AND STEREOCHEMICAL OUTCOME IN THE TANDEM WITTIG-OXY-COPE SEQUENCE OF ALLYL cis-5-METHYL-2-CYCLOHEXENYL ETHER

Article abstract of DOI:10.1016/S0040-4039(00)87746-1

The titled sigmatropic sequence proceeds with complete net retention of configuration, and surprisingly, suffers from a regiochemical complication arising mainly from the unexpected competition of the (2,3)- vs. (1,2)-shift in the Wittig process, as revealed by the use of the deuterium-labeled substrate.