Cover Feature: Single‐Step Glycosylations with 13C‐Labelled Sulfoxide Donors: A Low‐Temperature NMR Cartography of the Distinguishing Mechanistic Intermediates (Chem. Eur. J. 6/2021). Issue 6 (24th November 2020)

• Record Type: Journal Article
• Authors: Santana, Andrés G.; Montalvillo‐Jiménez, Laura; Díaz‐Casado, Laura; Mann, Enrique; Jiménez‐Barbero, Jesús; Gómez, Ana M.; Asensio, Juan Luis
• Is Part Of: Chemistry. Volume 27:Issue 6(2021)
• Page Start: 1862
• Page End: 1862
• Publication Date: 2020-11-24
• Subjects: carbohydrates -- glycosylation -- isotopic labelling -- NMR spectroscopy -- reaction mechanisms; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202004805
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract : The mechanistic study of one‐step sulfoxide glycosylations enabled by the employment of 13 C‐labelled glycosyl‐donors and low‐temperature NMR revealed the internal dynamics between all reaction intermediates involved in this process, which are represented in the accompanying image as a molecular rollercoaster. The formation and stability of donor/acceptor sulfonium adducts, inherent to this particular experimental protocol, defines the scope of this synthetic methodology. More information can be found in the Full Paper by A. G. Santana, J. L. Asensio, et al. on page 2030 .