Base-free β-boration of α,β-unsaturated imines catalysed by Cu2O with concurrent enhancement of asymmetric induction
Calow, A.D.J.; Solé, C.; Whiting., A.; Fernández, E.
Professor Andrew Whiting email@example.com
The stereoselective synthesis of γ-aminoalcohols from the catalytic asymmetric β-boration of α,β-unsaturated imine precursors has been streamlined with the use of Cu2O as the catalyst, readily accessible (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl as the chiral ligand and no additional base. The new simplicity of the catalytic system has the added value of in situ formation of the imines, which allows access to cyclic and acyclic β-boryl imines. The reaction was followed by using in situ IR spectroscopy, which demonstrated the imine formation– β-boration sequence and that the new catalytic system is superior to those employed for this reaction previously.
Calow, A., Solé, C., Whiting., A., & Fernández, E. (2013). Base-free β-boration of α,β-unsaturated imines catalysed by Cu2O with concurrent enhancement of asymmetric induction. ChemCatChem, 5(8), 2233-2239. https://doi.org/10.1002/cctc.201300113
|Journal Article Type||Article|
|Publication Date||Aug 1, 2013|
|Deposit Date||Nov 22, 2013|
|Publicly Available Date||May 22, 2014|
|Peer Reviewed||Peer Reviewed|
|Keywords||Copper, Boron, IR spectroscopy, P ligands, Asymmetric catalysis.|
Accepted Journal Article
This is the peer reviewed version of the following article: Calow, A. D. J., Solé, C., Whiting, A. and Fernández, E. (2013), Base-Free β-Boration of α,β-Unsaturated Imines Catalysed by Cu2O with Concurrent Enhancement of Asymmetric Induction. ChemCatChem, 5 (8): 2233–2239, which has been published in final form at http://dx.doi.org/10.1002/cctc.201300113. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.