828253-40-3Relevant academic research and scientific papers
The role of proton shuttling mechanisms in solvent-free and catalyst-free acetalization reactions of imines
Lillo, Victor J.,Mansilla, Javier,Saá, José M.
supporting information, p. 4527 - 4536 (2018/06/29)
Proton transfer is central to the understanding of chemical processes. More so in addition reactions of the type NuH + E → Nu-EH taking place under solvent-free and catalyst-free conditions. Herein we show that the addition of alcohols or amines (the NuH component) to imine derivatives (the E component), in 1:1 ratio, under solvent-free and catalyst-free conditions, are efficient methods to access N,O and N,N-acetal derivatives. In addition, computational studies reveal that they are catalyzed reactions involving two or even three NuH molecules operating in a cooperative manner as H-bonded NuH?(NuH)n?NuH associates (many body effects) in the transition state through a concerted proton shuttling mechanism (addition of alcohols) or stepwise proton shuttling mechanism (addition of amines), thereby facilitating the key proton transfer step.
Diastereoselective preparation of novel tetrahydrooxazinones via heterocycloaddition of N-Boc, O-Me-acetals
Gizecki, Patricia,Ait Youcef, Ramzi,Poulard, Céline,Dhal, Robert,Dujardin, Gilles
, p. 9589 - 9592 (2007/10/03)
Under Lewis acid conditions, reaction of N-Boc, O-Me acetals with the (R)-(+)-O-vinyl-pantolactone does not lead to the expected dihydrooxazine, but to the corresponding tetrahydrooxazinone, as a result of the loss of the t-Bu group. A diastereoselective
