Premium
Cover Picture: Iodine( III )‐Mediated Preparations of Nitrogen‐Containing Sulfur Derivatives: Dramatic Influence of the Sulfur Oxidation State (Chem. Eur. J. 4/2004)
Author(s) -
Leca Dominique,
Song Kai,
Amatore Muriel,
Fensterbank Louis,
Lacôte Emmanuel,
Malacria Max
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200490011
Subject(s) - chemistry , diastereomer , sulfur , racemization , iodine , nitrogen atom , walden inversion , methanol , stereoselectivity , medicinal chemistry , nitrogen , stereochemistry , catalysis , organic chemistry , ring (chemistry)
The cover picture shows the iodine‐mediated one‐pot stereoselective synthesis of a chiral sulfonimidate starting from a sulfinamide in the presence of methanol. The X‐ray diffraction structure determination of the major diastereoisomer indicated that the reaction mainly occurred with retention of configuration, presumably through an early intermediate, which was transformed following two different pathways. Rearrangement via a four‐atom transition state afforded sulfonimidates with retention of configuration. A competitive three‐atom rearrangement would cause the partial racemization. A discussion of these proposals, as well as the synthesis of free sulfonimidates and a convenient preparation of sulfoximines and sulfonamides are described by Malacria et al. on p. 906 ff.