Synthesis, X-ray crystallography and computational studies concerning an oxadiazinone derived from D-camphor: A structural limitation of oxadiazinones as chiral auxiliaries

Tetrahedron Asymmetry

Volumn 16, Issue 5, 2005, Pages 1047-1053

  Squire, Michael D ^a   Davis, Ryan A ^a   Chianakas, Karah A ^a   Ferrence, Gregory M ^a   Standard, Jean M ^a   Hitchcock, Shawn R ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,4,5,6 TETRAHYDRO 5 METHYL 4 (1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPT 2 YL) 6 PHENYL 3 PROPIONYL 2H 1,3,4 OXADIAZIN 2 ONE; AMINE; IMINE; OXADIAZINONE; OXADIAZOLE DERIVATIVE; TITANIUM; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHIRALITY; CONFORMATIONAL TRANSITION; CYCLIZATION; DENSITY FUNCTIONAL THEORY; GAS; MATHEMATICAL ANALYSIS; MATHEMATICAL COMPUTING; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 14344251993     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.01.020     Document Type: Article

References (39)

1. S.R. Hitchcock, D.M. Casper, J.F. Vaughn, J.M. Finefield, G.M. Ferrence, and J.M. Esken J. Org. Chem. 69 2004 714 718
2. J.F. Vaughn, and S.R. Hitchcock Tetrahedron: Asymmetry 15 2004 3449 3455
3. D.M. Casper, and S.R. Hitchcock Tetrahedron: Asymmetry 14 2003 517 521
4. D.M. Casper, J.R. Burgeson, J.M. Esken, G.M. Ferrence, and S.R. Hitchcock Org. Lett. 4 2002 3739 3742
5. 3)] will be disclosed elsewhere
6. Trepanier, D. L.; Harris, J. N. U.S. Patent 3,377,345, 1968; Chem. Abstr. 1969, 70, 78026c
7. D.L. Trepanier, J.N. Eble, and G.H. Harris J. Med. Chem. 11 1968 357 361
8. F. Roussi, A. Chauveau, M. Bonin, L. Micouin, and H. Husson Synthesis 2000 1170
9. F. Roussi, M. Bonin, A. Chiaroni, L. Micouin, C. Riche, and H. Husson Tetrahedron Lett. 40 1999 3727 3730
10. D.A. Evans, and J.T. Starr J. Am. Chem. Soc. 125 2003 13531 13540
11. B.D. Dorsey, K.J. Plzak, and R.G. Ball Tetrahedron Lett. 34 1993 1851 1854
12. D.A. Evans, S.J. Miller, M.D. Ennis, and P.L. Ornstein J. Org. Chem. 57 1992 1067 1069
13. M. Nerz-Stormes, and E.R. Thornton J. Org. Chem. 56 1991 2489 2498
14. M. Nerz-Stormes, and E.R. Thornton Tetrahedron Lett. 27 1986 897 900
15. D.A. Evans, J. Bartroli, and T.L. Shih J. Am. Chem. Soc. 103 1981 2127 2129
16. M.J. Martinelli J. Org. Chem. 55 1990 5065 5073
17. D.A. Evans, K.T. Chapman, and J. Bisaha J. Am. Chem. Soc. 110 1988 1238 1256
18. C. Chapuis, and J. Jurczak Helv. Chim. Acta 70 1987 436 440
19. E. Nicolas, K.C. Russell, and V.J. Hruby J. Org. Chem. 58 1993 766 770
20. E. Ernesto Nicolas, K.C. Russell, J. Knollenberg, and V.J. Hruby J. Org. Chem. 58 1993 7565 7571
21. M.P. Sibi, L. Venkatraman, M. Liu, and C.P. Jasperse J. Am. Chem. Soc. 123 2001 8444 8445
22. O. Corminboeuf, L. Quaranta, P. Renaud, P. Liu, C.P. Jasperse, and M.P. Sibi Chem. Eur. J. 9 2003 28 35
23. L. Quaranta, O. Corminboeuf, and P. Renaud Org. Lett. 4 2002 39 42
24. S.R. Hitchcock, D.M. Casper, G.P. Nora, J.R. Blackburn, J.T. Bentley, and D.C. Taylor J. Heterocycl. Chem. 39 2002 823 828
25. E.W. Baxter, and A.B. Reitz Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents Org. React. 59 2002 3 714
26. R. Bolton, T.N. Danks, and J.M. Paul Tetrahedron Lett. 35 1994 3411 3412
27. Danks and co-workers noted that sterically hindered amines either require long reaction times to react with camphor or fail to yield product in significant amounts
28. D.G. Morris, and K.S. Ryder Synthesis 1997 620 622
29. F.S. Guziec Jr., and J.M. Russo Synthesis 1984 479 481
30. M.D. Squire, A. Burwell, G.M. Ferrence, and S.R. Hitchcock Tetrahedron: Asymmetry 13 2002 1849 1854
31. Caution. Many N-nitrosamines are potentially carcinogenic and should be handled with great care. For more information on N-nitrosamines, please see: P.D. Lawley Chemical Carcinogens C.D. Searle ACS Monograph 182 1984 American Chemical Society Washington, DC
32. Crystallographic data (excluding structure factors) for 7 has been deposited with the Cambridge Crystallographic Data Center as supplementary publication number CCDC 239755. Copies of this data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, UK [fax: +44 (0)12233 336033 or e-mail: deposit@ccdc.cam.ac.uk ]
33. Spartan 5.1 and Spartan 02, Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, California
34. PQS 3.1, Parallel Quantum Solutions, 2013 Green Acres, Suite A, Fayetteville, Arkansas
35. We have shown previously that the geometries of similar heterocycles are described better with the AM1 semiempirical method than with the PM3 semiempirical method. See: S.R. Hitchcock, G.P. Nora, D.M. Casper, M.D. Squire, C.D. Maroules, G.M. Ferrence, L.F. Szczepura, and J.M. Standard Tetrahedron 57 2001 9789 9798
36. F. Eckert, and A. Klamt AiChE J. 48 2002 369 385
37. Based on our previous studies, the enolate is believed to possess the (Z)-configuration. See Ref. 1a
38. 3-aldol adduct side chain was determined by evaluating the coupling constant of the aldol adduct. The coupling constant was 2 Hz or less in all examples, which suggests the syn-aldol configuration. See: D.A. Evans, J.V. Nelson, and T.R. Taber Top. Stereochem. 13 1982 1 115
39. Crystallographic data (excluding structure factors) for 8c has been deposited with the Cambridge Crystallographic Data Center as supplementary publication number CCDC 239756. Copies of this data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, UK [fax: +44 (0)12233 336033 or e-mail: deposit@ccdc.cam.ac.uk ]