An anomeric effect drives the regiospecific ring-opening of 1,3-oxazolidines under acetylating conditions
A series of oxazolidines derived from tris(hydroxymethyl)-aminomethane (TRIS; 1), have been prepared efficiently. Geometries optimized at the B3LYP/6-31G* level of theory, along with the crystal data of compounds 9 and 12 and NOESY correlations
Martinez, R. Fernando,Avalos, Martin,Babiano, Reyes,Cintas, Pedro,Jimenez, Jose L.,Light, Mark E.,Palacios, Juan C.,Perez, Esther M. S.
experimental part
p. 5263 - 5273
(2010/11/02)
Synthesis and stereochemistry of some 1,3-oxazolidine systems based on TRIS (α,α,α-trimethylolaminomethane) and related aminopolyols skeleton. Part 2: 1-Aza-3,7-dioxabicyclo[3.3,0]octanes
The reaction of TRIS with equivalent amounts of two carbonyl compounds is shown to afford, diastereoselectively, the title compounds. The results are discussed as a synthetic strategy and the stereochemistry is supported by theoretical calculations and high resolution NMR data.
Genotoxicity in oxazolidine derivatives: influence of the nitro group
Tris-(hydroxymethyl)-aminomethane reacts with various aromatic or heterocyclic aldehydes, leading to new mono- or bicyclic oxazolidine derivatives.The importance of molecular surroundings of the nitro group has been evaluated by the genotoxic study of syn