Stereoselective cyanosilylation reactions in hindered cyclic ketones

Synlett

Volumn , Issue 9, 2004, Pages 1631-1633

  Moloney, Mark G ^a   Yaqoob, Muhammad ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Cyanohydrin; Diastereoselectivity; Ketones

Indexed keywords

KETONE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; CHEMICAL REACTION; REACTION ANALYSIS; SILYLATION; STEREOCHEMISTRY;

EID: 3943071027     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829534     Document Type: Article

References (26)

1. Moloney, M. G.; Trippier, P. C.; Yaqoob, M.; Wang, Z. Current Drug Discovery Technologies 2004, 1, submitted.
2. Bulger, P. G.; Moloney, M. G.; Trippier, P. C. Org. Biomol. Chem. 2003, 1, 3726.
3. Bulger, P. G.; Moloney, M. G.; Trippier, P. C. Synlett 2002, 1871.
4. Wang, Z.; Moloney, M. G. Tetrahedron Lett. 2002, 43, 9629.
5. Andrews, M. D.; Brewster, A. G.; Crapnell, K. M.; Ibbett, A. J.; Jones, T.; Moloney, M. G.; Prout, C. K.; Watkin, D. J. Chem. Soc., Perkin Trans. 1 1998, 223.
6. Andrews, M. D.; Brewster, A. G.; Chuhan, J.; Ibbett, A. J.; Moloney, M. G.; Prout, K.; Watkin, D. Synthesis 1997, 305.
7. Evans, D. A.; Truesdale, L. K.; Carroll, G. L. J. Chem Soc., Chem. Commun. 1973, 55.
8. Gregory, R. H. J. Chem. Rev. 1999, 99, 3649.
9. North, M. Synlett 1993, 807.
10. North, M. Tetrahedron: Asymmetry 2003, 14, 147.
11. Shen, Y. C.; Feng, X. M.; Li, Y.; Zhang, G. L.; Jiang, Y. Z. Tetrahedron 2003, 59, 5667.
12. Chen, F. X.; Feng, X. M.; Qin, B.; Zhang, G. L.; Jiang, Y. Z. Synlett 2003, 558.
13. Yadav, J. S.; Reddy, B. V. S.; Reddy, M. S.; Prasad, A. R. Tetrahedron Lett. 2002, 43, 9703.
14. Shen, Y. C.; Feng, X. M.; Li, Y.; Zhang, G. L.; Jiang, Y. Z. Synlett 2002, 793.
15. Bandini, M.; Cozzi, P. G.; Garelli, A.; Melchiorre, P.; Umani-Ronchi, A. Eur. J. Org. Chem. 2002, 3243.
16. Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. Tetrahedron Lett. 2001, 42, 3041.
17. Flores-Morales, V.; Fernandez-Zertuche, M.; Ordonez, M. Tetrahedron: Asymmetry 2003, 14, 2693.
18. Ohnuma, T.; Hata, N.; Fujiwara, H.; Ban, Y. J. Org. Chem. 1982, 47, 4713.
19. 5) and the mixture was stirred at r.t. (or 90°C for tetramic acid 2) for 24 h (6 h for compound 9). The crude product was immediately purified by flash chromatography using a petroleum ether-EtOAc eluant.
20. All new compounds gave satisfactory spectroscopic and high-resolution mass spectrometric or analytical data.
21. 1H NMR spectroscopy: for 6a at δ = 2.9 and 3.4 ppm (J = 13.6 Hz) and for 7a, the benzylic resonances appeared as a dd at δ = 2.5 and 3.6 ppm (J = 13.2 Hz).
22. The reaction of 5b differs from the earlier cases, since it exists exclusively as the enol tautomer, and product 6b/7b was not stable.
23. 13C nitrile resonances for the two disatereomers of 4a were at δ = 120.16 and 118.99 ppm, for 4b were at δ = 122.32 and 119.32 ppm, and for 6a and 7a were at δ = 119.08 and 118.86 ppm. For cyanohydrin 10, the corresponding values were 114.8 and 114.9 ppm, and for the single diastereomers 11 and 13, the values were 115.0 and 116.2 ppm.
24. Chikashita, H.; Ishibaba, M.; Ori, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1988, 61, 3637.
25. Andrews, M. D.; Brewster, A. G.; Moloney, M. G. J. Chem. Soc., Perkin Trans. 1 2002, 80.
26. Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746.