Amino acid derived thiane oxide and dioxide systems as disposable templates: Synthesis of α-amino ketones, anti-amino alcohols and an amino cyclopentenone

Tetrahedron Letters

Volumn 37, Issue 41, 1996, Pages 7457-7460

  Gamble, Mark P ^a   Giblin, Gerard M P ^b   Montana, John G ^c   O'Brien, Peter ^a   Ockendon, Timothy P ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c Chiroscience Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; CYCLOPENTENONE DERIVATIVE; KETONE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 16044364084     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01610-3     Document Type: Article

References (22)

1. 1. Guo, Z-X.; Schaeffer, M. J; Taylor, R. J. K. J. Chem. Soc., Chem. Commun., 1993, 874.
2. 2. Gamble, M. P.; Giblin, G. M. P.; Taylor, R. J. K. Syntett, 1995, 779.
3. 3. For leading references, see: Pauly, R.; Sasaki, N. A.; Potier, P. Tetrahedron Lett., 1994, 35, 237.
4. 4. Paquette, L. A. Org. React., 1977, 25, 1; Clough, J. M. in Comprehensive Organic Synthesis, ed. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991, vol. 3, chapter 3.8. See also reference 1.
5. 7m^4. Paquette, L. A. Org. React., 1977, 25, 1; Clough, J. M. in Comprehensive Organic Synthesis, ed. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991, vol. 3, chapter 3.8. See also reference 1.
6. 5. Grumann, A.; Marley, H.; Taylor, R. J. K. Tetrahedron Lett., 1995, 36, 7767.
7. 6. For other examples of this strategy, see: Armer, R.; Begley, M. J.; Cox, P. J.; Persad, A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1, 1993, 3105; Hayashi, T. Tetrahedron Lett., 1991, 32, 5369.
8. 6. For other examples of this strategy, see: Armer, R.; Begley, M. J.; Cox, P. J.; Persad, A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1, 1993, 3105; Hayashi, T. Tetrahedron Lett., 1991, 32, 5369.
9. 7. Yang, T-K.; Lee, D-S. in Encyclopedia of Reagents for Organic Synthesis, ed-in-chief Paquette, L. A. John Wiley & Sons, New York, 1995, vol. 6, p. 4401.
10. 8. All new compounds were characterised by NMR, CHN analysis or high resolution mass spectrometry.
11. 9. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett., 1984, 25, 1071.
12. 10. Treatment of 1 with 2.2 equiv of KHMDS at -78 °C followed by warming to room temperature over 5 h and stirring for 3 h gave an 88% crude yield of ketone 3 {[α]D-9-0 (c 0.3 in acetone}. Reproducible recrystallisation gave enantiomerically enriched 3 {[α]D-61.3 (c 0.3 in acetone); ∼ 50% ee}.
13. 11. Cyclic amino ketones of this type are usually reduced to syn amino alcohols: Melillo, D. G.; Larsen, R. D.; Mathre, D. J.; Shukis, W. F.; Wood, A. W.; Colleluori, J. R. J. Org. Chem., 1987, 52, 5143.
14. 12. The expected (see reference 11) syn stereochemistry was assigned using NOE experiments.
15. 13. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem., 1969, 34, 2543.
16. 14. We are grateful to Dr M. H. Moore and Mr L. Cronin for carrying out the X-ray crystallography.
17. 15. The syn selectivity of the reduction was also identified by sulfur oxidation of syn,syn-8 to sulfone syn-7.
18. 16. Zoller, U. in The Chemistry of Sulphones and Sulphoxides, ed. Patai, S. John Wiley & Sons, New York, 1988, chapter 9, p. 379.
19. 17. Aube, J.; Wolfe, M. S.; Yantiss, R. K.; Cook, S. M.; Takusagawa, F. Synth. Commun., 1992, 22, 3003.
20. 18. Kolenbrander, H. M. Can. J. Chem., 1969, 47, 327.
21. 19. Alkylation of 3 using potassium carbonate and benzyl bromide (under equilibrating conditions) generated a single diastereoisomer of 21. (formula presented)
22. 20. For an alternative approach using pseudoephedrine as a chiral auxiliary, see: Myers, A. G.; Yoon, T. Tetrahedron Lett., 1995, 36, 9429.