New Enantiomerically Pure Allylboronic Esters in Allyl Additions: Synthesis and NMR Investigation of Intermediates

@inproceedings{Pietruszka2006NewEP,
  title={New Enantiomerically Pure Allylboronic Esters in Allyl Additions: Synthesis and NMR Investigation of Intermediates},
  author={J{\"o}rg Pietruszka and Niklas Schoene},
  year={2006}
}
Enantiomerically pure allylboronic esters 1 + 2 with a stereogenic center u to the boron moiety can be obtained by a sigmatropic rearrangement of boron containing allyl alcohols. Allyl additions with the new reagents are highly selective, which was shown via the direct measurement of the diastereoisomeric ratio of the intermediates 5 + 6 by characteristic NMR chemical shifts. The observations are not limited to ester containing reagents, but holds also true for hydrocarbon side-chains (e.g. in… CONTINUE READING