Avalos, M., Babiano, R., Cintas, P., Jimenez, J.L., Light, M.E., Palacios, J.C. and Perez, E.M.S. (2007) Chiral N-acyloxazolidines: synthesis, structure, and mechanistic insights. Journal of Organic Chemistry, 73 (2), 661-672. (doi:10.1021/jo702149m).
Abstract
A series of chiral imines derived from 1-amino-1-deoxyalditols such as D-glucamine, a rather unexplored raw material from the chiral pool, have been serendipitiously transformed into a novel family of N-acetyl-1,3-oxazolidines by means of an unexpected acetylation. The structure of these substances is supported by spectroscopic and crystallographic data. The acetylates also trigger a complex dynamic transformation, in which an initially configured trans oxazolidine converts into a more stable cis-configured derivative. Both isomers can also exist as rotational conformers (E,Z) as a consequence of the restricted rotation around the N-acetyl bond. The barriers to rotation have been determined by variable-temperature experiments. Overall, this transformation most likely involves the intermediacy of a chiral iminium ion, which has been documented in the synthesis of nitrogen heterocycles, thus explaining the experimental facts.
This record has no associated files available for download.
More information
Identifiers
Catalogue record
Export record
Altmetrics
Contributors
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.