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- Title
Base-Free β-Boration of α,β-Unsaturated Imines Catalysed by Cu<sub>2</sub>O with Concurrent Enhancement of Asymmetric Induction.
- Authors
Calow, Adam D. J.; Solé, Cristina; Whiting, Andrew; Fernández, Elena
- 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.
- Subjects
IMINE synthesis; ASYMMETRIC synthesis; COPPER spectra; AMINO alcohols; ALCOHOLS (Chemical class); CARBON compounds spectra; INFRARED spectroscopy; ACYCLIC acids
- Publication
ChemCatChem, 2013, Vol 5, Issue 8, p2233
- ISSN
1867-3880
- Publication type
Article
- DOI
10.1002/cctc.201300113