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.

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 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.

Citation

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
• Print ISSN: 1477-0520
• Electronic ISSN: 1477-0539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 13
• Issue: 18
• Pages: 5122-5130
• DOI: https://doi.org/10.1039/c4ob02657h
• Public URL: https://durham-repository.worktribe.com/output/1413042