Preparation of racemic and enantiopure arenesulfonimidoyl azoles - New compounds chiral on sulfur

Article abstract of DOI:10.1080/10426509908037031

The novel arenesulfonimidoyl imidazoles 7a-j and nitrotriazoles 9d-j were obtained in good yield from the corresponding arenesulfonimidoyl chlorides 6a-j. The reaction of optically pure sulfonimidoyl chlorides 6 with imidazole resulted in the first reported optically active arenesulfonimidoyl imidazoles 7 with high enantiomeric purities (ee up to >99%); the stereochemical course of the reaction (inversion or retention at sulfur) is shown to be strongly dependent on the aryl substituent. By contrast, the analogous reaction of optically pure compounds 6 with 3-nitro-1,2,4-triazole led to racemic arenesulfonimidoyl nitrotriazoles 9. Optically active compounds of this type, (S)-9f (ee 99%) and (R)-9f (ee 92%), were obtained by semi-preparative chiral HPLC. The optically active arenesulfonimidoyl imidazolium salt (R_S,R_C)-8j was prepared by diastereoselective methylation (de >90%) of the optically pure imidazole derivative (R_S,R_C)-7j.

Full text of DOI:10.1080/10426509908037031

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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PREPARATION OF RACEMIC
AND ENANTIOPURE
ARENESULFONIMIDOYL AZOLES
- NEW COMPOUNDS CHIRAL ON
SULFUR
Ralph Kluge a b , Heiko Hocke a , Manfred Schulz a
Frank Schilke a
a Martin-Luther-Universität Halle-Wittenberg,
&
Institut für Organische Chemie Merseburg, D-06099,
Halle, Germany
b Martin-Luther-Universität Halle-Wittenberg,
Institut für Organische Chemie, Kurt-Mothes-Str. 2,
D-06120, Halle, Germany
Published online: 24 Sep 2006.
To cite this article: Ralph Kluge , Heiko Hocke , Manfred Schulz & Frank Schilke
(1999) PREPARATION OF RACEMIC AND ENANTIOPURE ARENESULFONIMIDOYL AZOLES -
NEW COMPOUNDS CHIRAL ON SULFUR, Phosphorus, Sulfur, and Silicon and the Related
Elements, 149:1, 179-206, DOI: 10.1080/10426509908037031
To link to this article: http://dx.doi.org/10.1080/10426509908037031
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