Stereoselective synthesis of 2,5-disubstituted-1,4-oxathiane S-oxides

Organic and Biomolecular Chemistry

Volumn 3, Issue 3, 2005, Pages 404-406

  Bedford, Simon T ^a   Grainger, Richard S ^a   Steed, Jonathan W ^b   Tisselli, Patrizia ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

^b DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ATOMS; COLUMN CHROMATOGRAPHY; HYDROGEN; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; PHASE TRANSITIONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY ANALYSIS; XYLENE;

CYCLIZATION; SULFENIC ACID; SULFOXIDES; THERMOLYSIS;

OXIDES;

SINGLE HETEROCYCLIC RINGS; SULFOXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HETEROCYCLIC COMPOUNDS, 1-RING; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFOXIDES;

EID: 14244255857     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b415529g     Document Type: Article

References (15)

1. J. W. Cubbage, Y. Guo, R. D. McCulla and W. S. Jenks, J. Org. Cham., 2001, 66, 8722 and references therein.
2. S. Braverman, in The Chemistry of Sulfenic Acids and their Deivatives; ed. S. Patai, Wiley, New York, 1990, p. 311.
3. (a) D. N. Jones, D. R. Hill, D. A. Lewton and C. Sheppard, J. Chem. Soc., Perkin Trans. 1, 1977, 1574;
4. (b) D. N. Jones, in Perspectives in the Organic Chemistry of Sulfur, ed. B. Zwanenburg and A. J. H. Klunder, Elsevier, New York, 1987, p. 189.
5. R. S. Grainger, P. Tisselli and J. W. Steed, Org. Biomol. Chem., 2004, 2, 151.
6. The intramolecular addition of the sulfenic acid 10 to the diene is a reversible process, and the ratio of 6: 7 we believe is a reflection of their relative thermodynamic stability.
7. M. Reggelin and C. Zur, Synthesis, 2000, 1.
8. The synthesis of morpholine N-oxides by cyclisation of a hydroxylamine onto a pendant double bond by analogous chemistry (Cope elimination/reverse-Cope elimination) has recently been reported: I. A. O'Neil, E. Cleator, V. E. Ramos, A. P. Chorlton and D. J. Tapolczay, Tetrahedron Lett., 2004, 45, 3655.
9. Reviews on the preparation and application of β-ketosulfoxides: (a) M. Carmen Carreño, Chem. Rev., 1995, 95, 1717;
10. (b) G. Solladie, and M. Carmen Carreno, in Organosulfur Chemistry, Synthetic Aspects, ed. P. Page, Academic Press, New York, 1995, p. 1.
11. All chiral compounds used in this study are racemic.
12. E. Juaristi and M. Ordoñez, in Organosulfur Chemistry, Synthetic and Stereochemical Aspects, ed. P. Page, Academic Press, San Diego, 1998, p. 63.
13. 1H NMR of 24a or 25a upon cooling to -60°C.
14. J. C. Carretero, J. L. Garcia Ruano and J. H. Rodriguez, Tetrahedron Lett., 1984, 25, 3029.
15. R. Bell, P. D. Cottam, J. Davies and D. N. Jones, J. Chem. Soc., Perkin Trans. 1, 1981, 2106.