PREPARATION OF RACEMIC AND ENANTIOPURE ARENESULFONIMIDOYL AZOLES - NEW COMPOUNDS CHIRAL ON SULFUR
Authors:
- 1 January 1999
- journal article
- research article
- Published by Taylor & Francis in Phosphorus, Sulfur, and Silicon and the Related Elements
- Vol. 149 (1) , 179-206
Abstract
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.Keywords
This publication has 24 references indexed in Scilit:
- 2-Amino-2-deoxyhexoses as chiral educts for hydroxylated indolizidines. Synthesis of (+)-castanospermine and (+)-6-epicastanospermineThe Journal of Organic Chemistry, 1991
- Preparation and reactions of sulfonimidoyl fluoridesThe Journal of Organic Chemistry, 1983
- Sulfonimidoyl chlorides by oxidation of sulfinamides with tert-butyl hypochloriteThe Journal of Organic Chemistry, 1979
- Preparation and reactions of sulfonimidoyl chloridesThe Journal of Organic Chemistry, 1979
- Stereochemistry of sulfur compounds. VII. Course of substitution at sulfur attached to four different ligandsJournal of the American Chemical Society, 1974
- Chemistry of sulfoxides and related compounds. XXXIII. Stereochemistry of substitution at tetracoordinate hexavalent sulfur. Nucleophilic reactions at sulfur in sulfonimidoyl compoundsJournal of the American Chemical Society, 1971
- Stereochemistry of sulfur compounds. I. Stereochemical reaction cycles involving an open chain sulfoxide, sulfimide, and sulfoximideJournal of the American Chemical Society, 1970
- Stereochemically nonrigid structuresAccounts of Chemical Research, 1970
- The stereochemical course of ester-amide interchange leading to optically active phosphinic and sulfinic amidesJournal of the American Chemical Society, 1968
- Neuere Methoden der präparativen organischen Chemie IV Synthesen mit heterocyclischen Amiden (Azoliden)Angewandte Chemie, 1962