First transfer of chirality in the Fritsch-Buttenberg-Wiechell rearrangement, via zinc carbenoids: A migration with retention of configuration

Article abstract of DOI:10.1016/S0040-4039(99)00090-8

Carbozincation of a metallated propargylic ether can lead to a gem bismetallic reagent with a good 1,3-diastereoselection. This latter can be relayed to a 1,4-diastereoselection, when the gembismetallic thus formed is monohalogenated to give a carbenoid which rearranges at room temperature.