Stereoselective synthesis of 2-substituted 3-azabicyclo[3.2.0]heptan-2-ones by [2+2]-cycloaddition of N-allyl-β-N-keteniminium salts derived from (R)-vinylglycinol

Tetrahedron Asymmetry

Volumn 11, Issue 13, 2000, Pages 2653-2659

  Delle Monache, Giuliano ^a   Misiti, Domenico ^b   Salvatore, Patrizia ^b   Zappia, Giovanni ^b   Pierini, Marco ^c  

^a CATHOLIC UNIVERSITY   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c Dip Scienze del Farmaco   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZYLOXYMETHYL 3 AZABICYCLO[3.2.0]HEPTAN 2 ONE; KETENE DERIVATIVE; N ALLYL BETA N KETENIMINIUM SALT; UNCLASSIFIED DRUG; VINYLGLYCINOL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CONFORMATION; CONTROLLED STUDY; MOLECULAR MECHANICS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034647972     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00237-8     Document Type: Article

References (41)

1. (a) Murakami, S.; Takemoto, T.; Shimizu, Z. J. Pharm. Soc. Jpn. 1953, 73, 1026.
2. (b) Konno, K.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1983, 24, 939.
3. (c) For a review, see: Parsons, A. F. Tetrahedron 1996, 4149.
4. See: (a) Excitatory Amino Acids; Simon, R. P., Ed.; Thieme Medical Publishers: New York, 1992. (b) Shinozaki, H.; Ishida, M.; Okamoto, T. Brain Res. 1986, 399, 395. (c) Maruyama, M.; Takeda, K. Brain Res. 1989, 504, 328.
5. See: (a) Excitatory Amino Acids; Simon, R. P., Ed.; Thieme Medical Publishers: New York, 1992. (b) Shinozaki, H.; Ishida, M.; Okamoto, T. Brain Res. 1986, 399, 395. (c) Maruyama, M.; Takeda, K. Brain Res. 1989, 504, 328.
6. See: (a) Excitatory Amino Acids; Simon, R. P., Ed.; Thieme Medical Publishers: New York, 1992. (b) Shinozaki, H.; Ishida, M.; Okamoto, T. Brain Res. 1986, 399, 395. (c) Maruyama, M.; Takeda, K. Brain Res. 1989, 504, 328.
7. Shinozaki, H.; Ishida, M.; Gotoh, Y.; Kwak, S. Brain Res. 1989, 503, 330.
8. (a) Helms, G. L.; Moore, R. E.; Niemczyra, W. P.; Patterson, G. M. L.; Tomer, K. B.; Gross, M. L. J. Org. Chem. 1988, 53, 1298.
9. (b) Benz, F.; Knüsel, F.; Nüesch, J.; Treischler, H.; Voser, W.; Nyfeher, R.; Keller-Schierlein, W. Helv. Chim. Acta 1974, 57, 2459.
10. (c) Keller-Jushen, C.; Kühn, M.; Loosli, H.-R.; Petcher, T. J.; Weber, H.; von Wartburg, A. Tetrahedron Lett. 1976, 4147.
11. (a) Liddell, J. R. Natural Prod. Rep. 1999, 16, 419.
12. (b) Takahata, H.; Momose, T. The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 44.
13. Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182.
14. (a) Sidani A.; Marchand-Brynaert, J.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1974, 13, 267; Org. Synth. 1990, 69, 199.
15. (a) Sidani A.; Marchand-Brynaert, J.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1974, 13, 267; Org. Synth. 1990, 69, 199.
16. (b) Markò, I.; Ronsmans, B., Hesbain-Frisque, A.-E.; Dumas, S.; Ghosez, L.; Ernst, B.; Grenter, H. J. Am. Chem. Soc. 1985, 107, 2192;
17. (c) Falmagne, J.-B.; Escudero, J.; Taleb-Sahraoni, S.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1981, 20, 879.
18. (d) Gobeaux, B.; Ghosez, L. Heterocycles 1989, 28, 29.
19. Snider, B. B. Chem. Rev. 1988, 88, 793.
20. (a) Houge, C.; Frisque-Hesbain, A-M.; Mockel, A.; Ghosez, L. J. Am. Chem. Soc. 1982, 104, 2920.
21. (b) Chen, L.; Ghosez, L. Tetrahedron Lett. 1990, 31, 4467.
22. (c) Chen, L.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1181.
23. (d) Genicot, C.; Ghosez, L. Tetrahedron Lett. 1992, 33, 7357.
24. Cholerton, T. J.; Collington, E. W.; Finch, H.; Williams, D. Tetrahedron Letters 1988, 29, 3369.
25. For an account of our work in this field, see: (a) Delle Monache, G.; Misiti, D.; Zappia, G. Tetrahedron: Asymmetry 1999, 10, 2961. (b) Delle Monache, G.; Di Giovanni, M. C.; Misiti, D.; Zappia, G. Tetrahedron: Asymmetry 1997, 8, 231. (c) Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Gazz. Chim. Ital. 1997, 127, 475. (d) Di Giovanni, M. C.; Misiti, D.; Villlani, C.; Zappia, G. Tetrahedron: Asymmetry 1996, 7, 2277. (e) Misiti, D.; Delle Monache, G.; Zappia, G. Liebigs Ann. Chem. 1996, 235.
26. For an account of our work in this field, see: (a) Delle Monache, G.; Misiti, D.; Zappia, G. Tetrahedron: Asymmetry 1999, 10, 2961. (b) Delle Monache, G.; Di Giovanni, M. C.; Misiti, D.; Zappia, G. Tetrahedron: Asymmetry 1997, 8, 231. (c) Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Gazz. Chim. Ital. 1997, 127, 475. (d) Di Giovanni, M. C.; Misiti, D.; Villlani, C.; Zappia, G. Tetrahedron: Asymmetry 1996, 7, 2277. (e) Misiti, D.; Delle Monache, G.; Zappia, G. Liebigs Ann. Chem. 1996, 235.
27. For an account of our work in this field, see: (a) Delle Monache, G.; Misiti, D.; Zappia, G. Tetrahedron: Asymmetry 1999, 10, 2961. (b) Delle Monache, G.; Di Giovanni, M. C.; Misiti, D.; Zappia, G. Tetrahedron: Asymmetry 1997, 8, 231. (c) Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Gazz. Chim. Ital. 1997, 127, 475. (d) Di Giovanni, M. C.; Misiti, D.; Villlani, C.; Zappia, G. Tetrahedron: Asymmetry 1996, 7, 2277. (e) Misiti, D.; Delle Monache, G.; Zappia, G. Liebigs Ann. Chem. 1996, 235.
28. For an account of our work in this field, see: (a) Delle Monache, G.; Misiti, D.; Zappia, G. Tetrahedron: Asymmetry 1999, 10, 2961. (b) Delle Monache, G.; Di Giovanni, M. C.; Misiti, D.; Zappia, G. Tetrahedron: Asymmetry 1997, 8, 231. (c) Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Gazz. Chim. Ital. 1997, 127, 475. (d) Di Giovanni, M. C.; Misiti, D.; Villlani, C.; Zappia, G. Tetrahedron: Asymmetry 1996, 7, 2277. (e) Misiti, D.; Delle Monache, G.; Zappia, G. Liebigs Ann. Chem. 1996, 235.
29. For an account of our work in this field, see: (a) Delle Monache, G.; Misiti, D.; Zappia, G. Tetrahedron: Asymmetry 1999, 10, 2961. (b) Delle Monache, G.; Di Giovanni, M. C.; Misiti, D.; Zappia, G. Tetrahedron: Asymmetry 1997, 8, 231. (c) Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Gazz. Chim. Ital. 1997, 127, 475. (d) Di Giovanni, M. C.; Misiti, D.; Villlani, C.; Zappia, G. Tetrahedron: Asymmetry 1996, 7, 2277. (e) Misiti, D.; Delle Monache, G.; Zappia, G. Liebigs Ann. Chem. 1996, 235.
30. Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. Synthesis 1988, 1707.
31. Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676.
32. Sakaitani, M.; Ohfune, Y. J. Org. Chem. 1990, 55, 870.
33. Bis alkylated product (3%) was isolated.
34. (a) Diago-Meseguer, J.; Palomo-Coll, A. L. Synthesis 1980, 547.
35. (b) Cabrè, J.; Palomo, A. L. Synthesis 1984, 413.
36. See, for instance: (a) Rey, M.; Roberts, S. M.; Dreiding, A. S.; Roussel, A.; Vanlierde, H.; Toppet, S.; Ghosez, L. Helvetica Chim. Acta 1982, 65, 703. (b) Snider, B. B.; Hui, R. A. H. F. J. Org. Chem. 1985, 50, 5167. (c) Snider, B. B.; Allentoff, A. J.; Walner, M. B. Tetrahedron 1990, 46, 8031.
37. See, for instance: (a) Rey, M.; Roberts, S. M.; Dreiding, A. S.; Roussel, A.; Vanlierde, H.; Toppet, S.; Ghosez, L. Helvetica Chim. Acta 1982, 65, 703. (b) Snider, B. B.; Hui, R. A. H. F. J. Org. Chem. 1985, 50, 5167. (c) Snider, B. B.; Allentoff, A. J.; Walner, M. B. Tetrahedron 1990, 46, 8031.
38. See, for instance: (a) Rey, M.; Roberts, S. M.; Dreiding, A. S.; Roussel, A.; Vanlierde, H.; Toppet, S.; Ghosez, L. Helvetica Chim. Acta 1982, 65, 703. (b) Snider, B. B.; Hui, R. A. H. F. J. Org. Chem. 1985, 50, 5167. (c) Snider, B. B.; Allentoff, A. J.; Walner, M. B. Tetrahedron 1990, 46, 8031.
39. Krow, G. R. Oganic Reactions 1993, 43, 251.
40. Batchmin of Macromodel Version 4.5 (Columbia Univ. New York), Amber* Force Field, united atoms, Monte Carlo stocastic algorithm with 5000 generated structures, minimization by PR conjugate gradient, energy window 12 kcal/mol. All the rotatable bonds were explored.
41. Structures generated by the conformational search were further optimized with the MMX force field (PC Model 4.0, Serena Software, Bloomington, IN). Energy comparison refers to MMX computed structures.