1260086-07-4Relevant academic research and scientific papers
Chemoselective CaO-mediated acylation of alcohols and amines in 2-methyltetrahydrofuran
Pace, Vittorio,Hoyos, Pilar,Alcántara, Andrés R.,Holzer, Wolfgang
, p. 905 - 910 (2013)
Calcium oxide is proposed as an innocuous acid scavenger for the chemoselective synthesis of amide- and ester-type compounds. Although these molecules have wide spread applications in organic and pharmaceutical chemistry, and a large number of routes have been designed for their synthesis, the development of more efficient and environmentally friendly acylation strategies remains an ongoing challenge. The use of CaO allows for the stoichiometric acylation of primary alcohols in the presence of phenols or tertiary alcohols; amines can also be subjected to acylation reactions in the presence of hydroxyl groups. Chirality is obtained through acylation if the starting material is an optically pure alcohol or if a chiral acylating agent is used. Furthermore, the use of 2-methyltetrahydrofuran (2-MeTHF), a more ecofriendly solvent, leads to maximized yields. This protocol is successfully applied to the synthesis of an interesting N-aryloxazolidin-2-one intermediate for the preparation of linezolid-type compounds.
First general route to substituted α-arylamino-α′ chloropropan-2-ones by oxidation of N-protected aminohalohydrins: The importance of disrupting hydrogen bond networks
Pace, Vittorio,Cabrera, Alvaro Cortes,Fernandez, Maria,Sinisterra, Jose V.,Alcantara, Andres R.
experimental part, p. 3545 - 3555 (2010/12/19)
The presence of a network of intra- and intermolecular hydrogen bonds in β-arylamino alcohols, confirmed by both IR spectroscopy and computer modeling, inhibits their oxidation to the corresponding α-amino ketones. A straightforward protocol, including highly regioselective protection (as carbamates) and subsequent oxidation with Dess-Martin periodinane, affords near quantitative yields of the desired N-protected ketones, which upon mild treatment with iodotrimethylsilane leads to a series of differently functionalized α-arylamino-α′-chloro ketones. Georg Thieme Verlag Stuttgart.
