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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.

One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived imines; functionalisation to homoallylic boronate carboxylate ester derivatives Thumbnail


Authors

A. Pujol

A.D.J. Calow

A.S. Batsanov



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

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