Chiral synthesis via organoboranes. 31. A simple synthesis of enantiomerically pure (Z)- and (E)-alkenes, (Z)-RCH=CHR* and (E)-RCH=CHR*

Article abstract of DOI:10.1016/S0957-4166(00)80049-X

The monoisopinocampheylorganylboranes, IpcR*BH, readily available in purities ≥ 99% ee by the asymmetric hydroboration of alkenes with monoisopinocampheylborane, IpcBH₂ are easily transformed into enantiomerically pure (≥ 99% ee) (Z)- and (E)-alkenes. The generality of the procedure was demonstrated by synthesizing four each (Z)- and (E)-alkenes. This new procedure makes the enantiomerically pure compounds readily available and contributes another stage to the completion of our goal of providing a truly general asymmetric synthesis of pure enantiomers.