Ring-opening of chiral N-(3,4-dihydro-4-oxoquinazolin-3-yl)-substituted aziridines (Q*-substituted aziridines): Access to Q*-free chirons

Tetrahedron Letters

Volumn 39, Issue 5-6, 1998, Pages 497-500

  Atkinson, Robert S ^a   Ayscough, Andrew P ^b   Gattrell, William T ^a   Raynham, Tony M ^c  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

^b British Biotech Pharmaceuticals Ltd   (United Kingdom)

^c ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DIASTEREOISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0032576863     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10586-X     Document Type: Article

References (19)

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3. 3. Atkinson, R.S., Coogan, M.P. and Lochne, I.S.T., J. Chem. Soc., Perkin Trans., 1997, 897; Atkinson, R.S. and Tughan, G., ibid., 1987, 2803.
4. 3. Atkinson, R.S., Coogan, M.P. and Lochne, I.S.T., J. Chem. Soc., Perkin Trans., 1997, 897; Atkinson, R.S. and Tughan, G., ibid., 1987, 2803.
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6. 4. Tanner, D., Angew. Chem. Int. Ed. Engl., 1994, 33, 599; Osborn, H.M.I. and Sweeney, J., Tetrahedron: Asymmetry, 1997, 8, 1693.
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9. 6. Farthing, C.N., Baldwin, J.E., Russell, A.T., Scholfield, C.J. and Spivey, A.C., Tetrahedron Lett., 1996, 37, 3761, 5225.
10. 7. Osborn, H.M.I. and Sweeney, J.B., Tetrahedron Lett., 1994, 35, 2731.
11. 8. Evans, O.A., Faul, M.M., Bilodeau, M.T., Anderson, B.A. and Barnes, D.M., J. Am. Chem. Soc., 1993, 115, 5328; Li, Z., Conser, K.R. and Jacobsen, E.N., J. Am. Chem. Soc., 1993, 115, 5326.
12. 8. Evans, O.A., Faul, M.M., Bilodeau, M.T., Anderson, B.A. and Barnes, D.M., J. Am. Chem. Soc., 1993, 115, 5328; Li, Z., Conser, K.R. and Jacobsen, E.N., J. Am. Chem. Soc., 1993, 115, 5326.
13. 9. Analogous ring-opening reactions to those in Scheme 2 have been carried out using aziridine 3.
14. 10. Prepared as a single racemic diastereoisomer from indene and the corresponding 3-acetoxyamino-quinazolinone (Ulukanli, S., unpublished work).
15. 11. The possibility of chelation by the quinazolinone oxygen with magnesium, and hence assistance in the ring-opening, cannot be excluded.
16. -3. Programs: Siemens SMART and SAINT control and integration software, SHELXTL (Sheldrick, G.M., University of Göttingen, Germany). Further details of the crystal structure investigation can be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
17. 13. Atkinson, R.S., Kelly, B.J. and Williams, J., Tetrahedron, 1992, 48, 7713.
18. 14. Nomura, R., Matsuo, T. and Endo, T., J. Am. Chem. Soc., 1996, 118, 11666; see also Corey, E.J. and Zheng, G.Z., Tetrahedron Lett., 1997, 38, 2045.
19. 14. Nomura, R., Matsuo, T. and Endo, T., J. Am. Chem. Soc., 1996, 118, 11666; see also Corey, E.J. and Zheng, G.Z., Tetrahedron Lett., 1997, 38, 2045.