Benzothiazines in synthesis. Further studies of the intramolecular, stereoselective addition of sulfonimidoyl carbanions to α,β- unsaturated functional groups

Journal of Organic Chemistry

Volumn 74, Issue 8, 2009, Pages 3214-3216

  Harmata, Michael ^a   Rayanil, Kanok On ^a   Espejo, Vinson R ^a   Barnes, Charles L ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATION; ELECTRON-WITHDRAWING GROUPS; ELECTROPHILES; HIGH TEMPERATURES; MICHAEL ADDITIONS; NUCLEOPHILIC ADDITIONS; STEREO-SELECTIVE; STEREOSELECTIVE ADDITIONS; SULFOXIMINE; VERY LOW TEMPERATURES;

FUNCTIONAL GROUPS; OLEFINS;

STEREOSELECTIVITY;

BENZOTHIAZINE DERIVATIVE; ELECTROPHILE; FUNCTIONAL GROUP; SULFONE DERIVATIVE; SULFONIMIDOYL CARBANION; SULFOXIMINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ARYLATION; CHEMICAL STRUCTURE; CROSS LINKING; ELECTRON; HIGH TEMPERATURE; LOW TEMPERATURE; MICHAEL ADDITION; STEREOCHEMISTRY; SYNTHESIS;

ALKENES; ANIONS; BENZOTHIADIAZINES; CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONIUM COMPOUNDS;

EID: 65249155010     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900151d     Document Type: Article

References (10)

1. Eicher, T.; Haputmann, S.; Suschitzky, H. The Chemistry of Hetero cycles: Structure, Reactions, Syntheses and Applications, 2nd ed.; Wiley: Chichester, UK, 2003.
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3. Harmata, M.; Hong, X. J. Am. Chem. Soc. 2003, 125, 5754-5756.
4. (a) Harmata, M.; Hong, X.; Schreiner, P. R. J. Org. Chem. 2008, 73, 1290-1296.
5. (b) Harmata, M.; Hong, X. Tetrahedron Lett. 2005, 46, 3847-3849.
6. (a) Harmata, M.; Hong, X. Org. Lett. 2005, 7, 3581.
7. (b) Harmata, M.; Hong, X.; Barnes, C. L. Org. Lett. 2004, 6, 2201.
8. Bolm, C.; Hildebrand, J. P. Tetrahedron Lett. 1998, 39, 5731-5734.
9. During the course of our studies, we have found that the nature of the base, including the cation, has no effect on the stereochemical outcome of the reaction, at least with esters as the electron-withdrawing group. Details will be reported elsewhere.
10. 3 Whether this is true for other electron-withdrawing groups remains to be seen.