Generation and Cycloadditions of 2-(N-acylamino)-1-thia-1,3-dienes part III: Control of diastereoselectivity using homochiral auxiliaries

Tetrahedron

Volumn 54, Issue 13, 1998, Pages 3219-3234

  Bell, Andrew S ^b   Fishwick, Colin W G ^a   Reed, Jessica E ^a,c  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^c UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; N ACYLAMINO ACID;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; OPTICAL ROTATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032568425     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00067-2     Document Type: Article

References (39)

1. 1. a) Barnish, I. T.; Fishwick, C. W. G.; Hill, D.R.; C. Szantay, C. Tetrahedron Lett. 1989, 30, 4449.
2. b) Barnish, I. T.; Fishwick, C. W. G.; Hill, D. R.; C. Szantay, C. Tetrahedron 1989, 45, 6771.
3. c) Barnish, I. T.; Fishwick, C. W. G.; Hill, D. R.; C. Szantay, C. Tetrahedron 1989, 45, 7879.
4. d) Barnish, I. T.; Fishwick, C. W. G.; Hill, D. R.; Tetrahedron Lett. 1991, 32, 405.
5. 2. Recent reviews a) Oh, T.; Reilly, M. Org. Prep. Proc. Int. 1994, 26, 129-158
6. b) Fringuelli, F.; Taitchi, A.; Wenkert, E. Org. Prep. Proc. Int. 1990, 22, 131-165
7. c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Peragmon Press: New York 1990.
8. d) Paquette, L. A. Asymmetric Synthesis; Morrison, J. D.; Ed.; Academic Press: New York 1984 Chapter 7.
9. 3. a) Arce, E.; Carreno, M. C.; Cid, M. B.; Ruano, J. L. G. J. Org. Chem. 1994, 59, 3421.
10. b) Winterfeldt, E.; Chem. Rev. 1993, 93, 827.
11. c) Adams, H.; Jones, D. N.; Aversa, M. C.; Bonacorsi, P.; Gianneto, P. Tetrahedron Lett. 1993, 34, 6481.
12. d) Tripathy, R.; Carrol, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1991, 110, 7630.
13. e) Lassen, D. S.; Stoodley, R. J. J. Chem. Soc. Perkins Trans. 1 1990, 1339.
14. f) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625.
15. 4. a) Defoin, A.; Broillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109.
16. b) Oppolzer, W.; Rodrigez, I.; Starkemann, C.; Walther, E. Tetrahedron Lett. 1990, 31, 5019.
17. c) Waldner, A. Tetrahedron Lett. 1989, 30, 3061-3064.
18. d) Evans, D.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
19. 5. a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
20. b) Deloux, L.; Srebnik, M.; Chem. Rev. 1993, 93, 763.
21. 6. Waldmann, H. Synthesis 1994, 535.
22. 7. Boger, D. L.; Weinreb, S. N. Hetero Dels-Alder Methodology in Organic Synthesis. Organic Chemistry Vol. 47 Academic Press 1987.
23. 8. a) Motoko, S.; Saito, T.; Karasaka, T.; Kato, H.; Matsushita, T.; Hayashibe, S. J.; J. Chem. Soc. Perkins Trans. 1, 1991, 2281.
24. b) Saito, T.; Karasaka, T.; Fujii, H.; Furuno, E.; Suda, H.; Kobayashi, K.; J. Chem. Soc. Perkins Trans. 1, 1994, 1359.
25. c) Takahashi, T.; Kurose, N.; Koizume, T. Heterocycles 1993, 36, 1501.
26. d) Marchand, A.; Mauger, D.; Guignant, A.; Pradere, J. P. Tetrahedron Asymmetry, 1995, 6, 853.
27. 9. Bell, A. S.; Fishwick, C. W. G; Reed, J. E. Tetrahedron Lett. 1996, 37, 123.
28. 10. a) Ramberg, L.; Backlund, B. Ark. Kem. Mineral. Geol. 1940, 13A, 50,
29. b) Chen, T. B. R. A.; Burger, J. J.; de Waard, E. R. Tetrahedron Lett. 1977, 18, 4527.
30. c) Burger, J. J.; Chen, T. B. R. A.; de Waard, E. R.; Huisman, H. O. Tetrahedron 1981, 37, 417.
31. d) Meyers, C. Y.; Malte, A. M.; Mathews, W. S. J. Am. Chem. Soc. 1986, 91, 7510.
32. e) Jeffery, S. M.; Sutherland, A. G.; Pyke, S. M.; Powell, A. K.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1, 1993, 2317.
33. f) Chan, T. L.; Hung, C. W.; Man, T. O.; Leung, M. K. J. Chem. Soc., Chem., Commun. 1994, 1971.
34. g) Cao, X. P.; Chan, T. L.; Chow, H. F.; Tu, J. J. Chem. Soc., Chem. Commun. 1995, 1297.
35. 11 Molecular models were constructed on Silicon Graphics Indigo using Macro Model v3.0, developed by Professor W.C. Still. All models were optimised using AM1 Hamiltonian in MOPAC v6.0 which was optimised for parallel computation using a Silicon Graphics Challenge eight processor parallel computer. Transition structures were located via the SADDLE routine in MOPAC and optimised via the TS routine. Transition structures were characterised using FORCE within MOPAC.
36. 12. Conversion of the homochiral acids to acid chlorides was completed using catalytic DMF and thionyl chloride. Excess thionyl chloride was removed in vacuo and the acid chlorides used crude. N-phenyl maleimide was the dienophile.
37. 13. Tornetta, B.; Scapini, F.; Guerrera, F.; Bernardini, A. Boll. Sedute. Accad. Gioenia. Sci. Natur. Catania. 1970, 10, 353. Chem. Abs. 1973, 78, 620.
38. 13. Tornetta, B.; Scapini, F.; Guerrera, F.; Bernardini, A. Boll. Sedute. Accad. Gioenia. Sci. Natur. Catania. 1970, 10, 353. Chem. Abs. 1973, 78, 620.
39. 14. Hill, D. R. Ph.D. Thesis University of Leeds 1990.