One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived imines; functionalisation to homoallylic boronate carboxylate ester derivatives
Pujol, A.; Calow, A.D.J.; Batsanov, A.S.; Whiting, A.
Professor Andrew Whiting firstname.lastname@example.org
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 a derivatisation process was required to give more stable compounds. The best synthetic derivatisation pathway involved the synthesis of homoallylboronates using an in situ imine hydrolysis-Wittig olefination protocol, resulting in stable analogues from which enatiomeric excess could be readily measured. The resulting homoallylic boronate esters also provided an opportunity to introduce a second boryl unit in a stereoselective manner which will be useful for transformation into other functionalities leading to key building blocks for the synthesis of multi-functional, chiral compounds.
Pujol, A., Calow, A., Batsanov, A., & Whiting, A. (2015). One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived imines; functionalisation to homoallylic boronate carboxylate ester derivatives. Organic and Biomolecular Chemistry, 13(18), 5122-5130. https://doi.org/10.1039/c4ob02657h
|Journal Article Type||Article|
|Acceptance Date||Mar 26, 2015|
|Publication Date||May 14, 2015|
|Deposit Date||Mar 26, 2015|
|Publicly Available Date||Mar 24, 2016|
|Journal||Organic and Biomolecular Chemistry|
|Publisher||Royal Society of Chemistry|
|Peer Reviewed||Peer Reviewed|
Accepted Journal Article