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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.

Base-free β-boration of α,β-unsaturated imines catalysed by Cu2O with concurrent enhancement of asymmetric induction Thumbnail


Authors

A.D.J. Calow

C. Solé

E. Fernández



Abstract

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.

Citation

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 Mar 28, 2024
Journal ChemCatChem
Print ISSN 1867-3880
Electronic ISSN 1867-3899
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 5
Issue 8
Pages 2233-2239
DOI https://doi.org/10.1002/cctc.201300113
Keywords Copper, Boron, IR spectroscopy, P ligands, Asymmetric catalysis.

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Accepted Journal Article (779 Kb)
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Copyright Statement
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.





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