Unexpected nucleophilic participation and rearrangement of DBU in reactions with saccharin derivatives

Synthetic Communications

Volumn 33, Issue 11, 2003, Pages 1937-1941

  Bulman Page, Philip C ^a   Vahedi, Hooshang ^a   Bethell, Donald ^b   Barkley, James V ^b  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

DBU; Nucleophile

Indexed keywords

3 [3' (1'' AZEPIN 2'' ONYL)PROPYLAMINO] 1,2 BENZISOTHIAZOLE 1,1 DIOXIDE; BASE; SACCHARIN DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CRYSTALLIZATION; OXIDATION; REACTION ANALYSIS; THIN LAYER CHROMATOGRAPHY; X RAY CRYSTALLOGRAPHY;

EID: 0038244887     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120020208     Document Type: Article

References (6)

1. (a) Page, P.C.B.; Bethell, D.; Stocks, P.A.; Heer, J.P.; Graham, A.E.; Vahedi, H.; Healy, M.; Collington, E.W.; Andrews, D.M. Sulfur oxidation mediated by imine derivatives. Synlett 1997, 1355;
2. (b) Bethell, D.; Page, P.C.B.; Vahedi, H. Catalytic asymmetric oxidation of sulfides to sulfoxides mediated by chiral 3-substituted-1,2-benzisothiazole 1,1-dioxides. J. Org. Chem. 2000, 65, 6756.
3. (a) Page, P.C.B.; Heer, J.P.; Bethell, D.; Collington, E.W.; Andrews, D.M.; A new system for catalytic asymmetric oxidation of sulfides using a hydrogen peroxide based reagent. Tetrahedron Lett. 1994, 35, 9629;
4. (b) Page, P.C.B.; Heer, J.P.; Bethell, D.; Collington, E.W.; Andrews, D.M. Highly enantioselective catalytic asymmetric oxidation of sulfides using hydrogen peroxide. Synlett 1995, 773;
5. (c) Page, P.C.B.; Heer, J.P.; Bethell, D.; Collington, E.W.; Andrews, D.M.; Asymmetric sulfoxidation using [(3,3-dimethoxycamphoryl)sulfonyl] oxaziridine. Tetrahedron: Asymmetry 1995, 6, 2911.
6. Davis, F.A.; Towson, J.C.; Vashi, D.B.; Thimma Reddy, R.; McCauley, J.P., Jr.; Harakal, M.E.; Gosciniak, D.J. Chemistry of oxaziridines. 13. Synthesis, reactions, and properties of 3-substituted 1,2-benzisothiazole 1,1-dioxide oxides. J. Org. Chem. 1990, 55, 1254.