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Cover Feature: Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2‐Azidofuranoses, 2‐Fluorofuranoses and Methyl Furanosyl Uronates (Chem. Eur. J. 29/2019)
Author(s) -
van der Vorm Stefan,
Hansen Thomas,
van Rijssel Erwin R.,
Dekkers Rolf,
Madern Jerre M.,
Overkleeft Herman S.,
Filippov Dmitri V.,
van der Marel Gijsbert A.,
Codée Jeroen D. C.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901260
Subject(s) - oxocarbenium , chemistry , stereoselectivity , glycosylation , glycosyl , azide , energy landscape , stereochemistry , computational chemistry , ring (chemistry) , ion , organic chemistry , catalysis , biochemistry , nucleophile
Energy maps of the full conformational space of 5‐membered ring glycosyl oxocarbenium ions have been generated to probe the stereoelectronic effects of C‐2‐fluoride, C‐2‐azide and C‐4‐carboxylic acid ester substituents. The computational results describing the overall shape of the reactive intermediates were complemented by experiments to show that the vast majority of studied furanosides react in an 1,2‐ cis selective manner in S N 1‐type glycosylation reactions. More information can be found in the Full Paper by J. D. C. Codée et al. on page 7149.