Synthesis of chiral 3,4,5,6-tetrahydro-1,4-thiazin-2-ones (thiamorpholin-2-ones) - Novel heterocycles possessing enhanced carbonyl electrophilicity over their oxygen counterparts

Synlett

Volumn , Issue 19, 2006, Pages 3259-3262

  Drew, Michael G B ^a   Harwood, Laurence M ^a   Yan, Ran ^a  

^a UNIVERSITY OF READING   (United Kingdom)

Author keywords

1,4 thiazinone; Chiral; Thiamorpholinone

Indexed keywords

1,4 THIAZINONE; OXYGEN DERIVATIVE; THIAMORPHOLIN 2 ONE DERIVATIVE; THIOLACTONE; THIOMORPHOLINE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ELECTROPHILIC STRESS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 33845613129     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951548     Document Type: Article

References (19)

1. For recent communications, see: (a) Draffin, W. N.; Harwood, L. M. Synlett 2006, 857.
2. (b) Aldous, D. J.; Drew, M. G. B.; Draffin, W. N.; Hamelin, E. M.-N.; Harwood, L. M.; Thurairatnam, S. Synthesis 2005, 3271.
3. (c) Aldous, D. J.; Hamelin, E. M.-N.; Harwood, L. M.; Thurairatnam, S. Synlett 2001, 1841.
4. (d) Aldous, D. J.; Drew, M. G. B.; Hamelin, E. M.-N.; Harwood, L. M.; Jahans, A. B.; Thurairatnam, S. Synlett 2001, 1836; see also references cited therein.
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6. (b) Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S. M.; Watkin, D. J.; Williams, C. E. Tetrahedron 1998, 54, 6089.
7. A few reports of thiamorpholinones embedded within β-lactam structures have appeared: (a) Costerousse, G.; Cagniant, A.; Didierlaurent, S. Bull. Soc. Chim. Fr. 1989, 830.
8. (b) Hakimelahi, G. H.; Tsay, S.-C.; Ramezani, Z.; Hwu, J. R. Helv. Chim. Acta 1996, 79, 813.
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11. 2O (4:1) to furnish the title product as a pale yellow oil (56 mg, 61%).
12. 3).
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14. 13 to R1 = 0.1039, wR2 = 0.1641. Atomic coordinates, bond lengths and angles and thermal parameters have been deposited with the Cambridge Crystallographic Database Service. Please quote reference number CCDC 617867.
15. For example, see: (a) Drew, M. G. B.; Harwood, L. M.; Price, D. W.; Park, G. Tetrahedron Lett. 2000, 5077.
16. (b) Drew, M. G. B.; Harwood, L. M.; Park, G.; Price, D. W.; Tyler, S. N. G.; Park, C. R.; Gho, S. G. Tetrahedron 2001, 57, 5641.
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19. Sheldrick, G. M. Program for Crystal Structure Refinement; University of Göttingen: Germany, 1993.