title: One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived imines; functionalisation to homoallylic boronate carboxylate ester derivatives.
abstract: The β-borylation reaction of α,β-unsaturated aldehyde-derived imines, formed in situ, has been studied using a one-pot methodology, as a route to β-boryl aldehydes. The instability of the β-boryl aldehydes meant that derivatisation was required and routes to both acetal derivatives and homoallylic boronates were examined. β-Boryl acetals were also found to be unstable, however, the formation of homoallylic boronate derivatives using an in situ imine hydrolysis-Wittig olefination protocol was found to be suitable, resulting in an efficient synthesis with high enantiomeric excesses.
authors.affiliation: Centre for Sustainable Chemical Processes, Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, UK. andy.whiting@durham.ac.uk.
authors.forename: Alba
authors.initials: A
authors.lastname: Pujol
authors.forename: Adam D J
authors.initials: AD
authors.lastname: Calow
authors.forename: Andrei S
authors.initials: AS
authors.lastname: Batsanov
authors.forename: Andrew
authors.initials: A
authors.lastname: Whiting