27760-62-9Relevant academic research and scientific papers
Understanding α,β-unsaturated imine formation from amine additions to α,β-unsaturated aldehydes and ketones: An analytical and theoretical investigation
Calow, Adam D. J.,Carbó, Jorge J.,Cid, Jessica,Fernández, Elena,Whiting, Andrew
, p. 5163 - 5172 (2014)
A combination of in situ IR spectroscopy (ReactIR) and DFT calculations have been used to understand what factors govern the selectivity in the addition of primary amines to α,β-unsaturated aldehydes and ketones, i.e., 1,2- versus 1,4-addition. It has been found that the 1,2-addition products (α,β-unsaturated imines following addition and elimination) usually predominate for most systems. However, exceptions, such as methyl vinyl ketone, selectively give 1,4-addition products. This has been rationalized by DFT calculations that show that major conformational effects are involved, controlled mainly by steric effects of carbonyl substituents, resulting in a model that provides simple and predictable preparation of α,β- unsaturated imines for in situ utilization in synthesis.
Novel transformation of α,β-unsaturated aldehydes and ketones into γ-amino alcohols or 1,3-oxazines via a 4 or 5 step, one-pot sequence
Calow, Adam D. J.,Batsanov, Andrei S.,Fernández, Elena,Solé, Cristina,Whiting, Andrew
, p. 11401 - 11403 (2013/01/15)
An efficient, 4-step, one-pot, highly stereoselective route to γ-amino alcohols has been developed via an in situ α,β- unsaturated imine formation, β-boration, reduction (CN) and oxidation (C-B) sequence and especially for certain water-soluble γ-amino alcohols, a further step can be added to directly access the corresponding 1,3-oxazine derivatives.
