Highly regio- and stereoselective iodocyclization of chiral 3- alkoxycarbonyl-4-propenyl-2,2-dimethyl-1,3-oxazolidines: A computational investigation

Tetrahedron Asymmetry

Volumn 10, Issue 6, 1999, Pages 1135-1143

  Jordá Gregori, Juan Miquel ^a   González Rosende, M Eugenia ^a   Sepúlveda Arques, José ^a   Galeazzi, Roberta ^b   Orena, Mario ^b  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATIONAL TRANSITION; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 0038607281     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00084-1     Document Type: Article

References (39)

1. (a) Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. Chem. Soc., Perkin Trans. 1. 1986, 1345-1349.
2. (b) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. Tetrahedron 1987, 43, 4377-4383.
3. (c) Cardillo, G.; Orena, M. Pure Appl. Chem. 1988, 60, 1679-1688.
4. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321-3408.
5. (e) Orena, M. Amination Reactions Promoted by Electrophiles. In Houben-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds. Thieme: Stuttgart, 1995; Vol. E 21e, pp. 5291-5355.
6. (a) Pauls, H.; Fraser-Reid, B. J. Am. Chem. Soc. 1980, 102, 3956-3957.
7. (b) Overman, L. E.; McCready, R. J. Tetrahedron Lett. 1982, 23, 4887-4890.
8. (c) Georges, M.; MacKay, D.; Fraser-Reid, B. J. Am. Chem. Soc. 1982, 104, 1101-1103.
9. (d) Barlett, P. A.; Tanzella, D. J.; Barstow, J. F. Tetrahedron Lett. 1982, 23, 619-622.
10. (e) Parker, K. A.; O'Fee, R. J. Am. Chem. Soc. 1983, 105, 654-655.
11. (f) Kobayashi, S.; Isobe, T.; Ohno, M. Tetrahedron Lett. 1984, 25, 5079-5082.
12. (g) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. Chem. Lett. 1988, 43, 87-90.
13. (h) Kamiyama, K.; Urano, Y.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1987, 28, 3123-3126.
14. (i) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1987, 43, 2505-2512,
15. (j) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362.
16. (k) Guindon, Y.; Slassi, A.; Ghiro, E.; Bantle, G.; Jung, G. Tetrahedron Lett. 1992, 33, 4257-4260.
17. (l) Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Tetrahedron 1993, 49, 11321-11328.
18. Doboszewski, B.; Herdewijn, P. Tetrahedron 1996, 52, 1651-1668.
19. Rassu, G.; Zanardi, F.; Cornia, M.; Casiraghi, G. J. Chem. Soc., Perkin Trans. 1 1994, 2431-2437.
20. Marshall, J. A.; Beaudoin, S. J. Org. Chem. 1996, 61, 581-586.
21. Beaulieu, P. L.; Duceppe, J.-S.; Johnson C. J. Org. Chem. 1991, 56, 4196-4204.
22. No reaction was observed starting from both (R)-3-benzyloxycarbonyl-2,2-dimethyl-4-(1-propenyl)-1,3-oxazolidine and (E,R)-3-benzyloxycarbonyl-2,2-dimethyl-4-(2-ethoxycarbonylethenyl)-1,3- oxazolidine. This result was surprising, in comparison with those reported for analogous systems (see Ref. 2e and h), although an explanation seems rather difficult to find.
23. 2,3 3.5 Hz); whereas the (S)-configuration for the stereogenic center in the side chain was tentatively assigned from mechanistic considerations, by assuming an anti-addition mechanism to the Z-double bond. (matrix presented) For recent references concerning 4-exo closure leading to oxetanes, see: (a) Galatsis, P.; Millan, S. D.; Nechala, P.; Ferguson, G. J. Org. Chem. 1994, 59, 6643-6651. (b) Barks, J. M.; Knight, D. W. Tetrahedron Lett. 1996, 35, 7259-7262. (c) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 36, 7667-7670. (d) Galatsis, P.; Millan, S. D.; Ferguson, G. J. Org. Chem. 1997, 62, 5048-5056.
24. 2,3 3.5 Hz); whereas the (S)-configuration for the stereogenic center in the side chain was tentatively assigned from mechanistic considerations, by assuming an anti-addition mechanism to the Z-double bond. (matrix presented) For recent references concerning 4-exo closure leading to oxetanes, see: (a) Galatsis, P.; Millan, S. D.; Nechala, P.; Ferguson, G. J. Org. Chem. 1994, 59, 6643-6651. (b) Barks, J. M.; Knight, D. W. Tetrahedron Lett. 1996, 35, 7259-7262. (c) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 36, 7667-7670. (d) Galatsis, P.; Millan, S. D.; Ferguson, G. J. Org. Chem. 1997, 62, 5048-5056.
25. 2,3 3.5 Hz); whereas the (S)-configuration for the stereogenic center in the side chain was tentatively assigned from mechanistic considerations, by assuming an anti-addition mechanism to the Z-double bond. (matrix presented) For recent references concerning 4-exo closure leading to oxetanes, see: (a) Galatsis, P.; Millan, S. D.; Nechala, P.; Ferguson, G. J. Org. Chem. 1994, 59, 6643-6651. (b) Barks, J. M.; Knight, D. W. Tetrahedron Lett. 1996, 35, 7259-7262. (c) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 36, 7667-7670. (d) Galatsis, P.; Millan, S. D.; Ferguson, G. J. Org. Chem. 1997, 62, 5048-5056.
26. 2,3 3.5 Hz); whereas the (S)-configuration for the stereogenic center in the side chain was tentatively assigned from mechanistic considerations, by assuming an anti-addition mechanism to the Z-double bond. (matrix presented) For recent references concerning 4-exo closure leading to oxetanes, see: (a) Galatsis, P.; Millan, S. D.; Nechala, P.; Ferguson, G. J. Org. Chem. 1994, 59, 6643-6651. (b) Barks, J. M.; Knight, D. W. Tetrahedron Lett. 1996, 35, 7259-7262. (c) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 36, 7667-7670. (d) Galatsis, P.; Millan, S. D.; Ferguson, G. J. Org. Chem. 1997, 62, 5048-5056.
27. Macromodel, version 5.5. For references, see: (a) Mahamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990. 11, 440-447. (b) Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765-784. (c) Goodman, J. M.; Still, W. C. J. Comput. Chem. 1991, 12, 1110-1114.
28. Macromodel, version 5.5. For references, see: (a) Mahamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990. 11, 440-447. (b) Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765-784. (c) Goodman, J. M.; Still, W. C. J. Comput. Chem. 1991, 12, 1110-1114.
29. Macromodel, version 5.5. For references, see: (a) Mahamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990. 11, 440-447. (b) Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765-784. (c) Goodman, J. M.; Still, W. C. J. Comput. Chem. 1991, 12, 1110-1114.
30. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736; Baldwin J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. Ibid. 1976, 736-738; Baldwin, J. E. Ibid. 1976, 738-741.
31. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736; Baldwin J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. Ibid. 1976, 736-738; Baldwin, J. E. Ibid. 1976, 738-741.
32. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736; Baldwin J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. Ibid. 1976, 736-738; Baldwin, J. E. Ibid. 1976, 738-741.
33. (a) Watanabe, M.; Okada, H.; Teshima, T.; Kakehi, A. Tetrahedron 1996, 52, 2827-2838.
34. (b) Yamabe, S.; Minato, T. Bull. Chem. Soc. Jpn. 1993, 66, 3339-3344.
35. Hyperchem package, release 5.1, available from Hypercube, Gainesville, Florida, USA.
36. (a) Chamberlin, A. R.; Mulholland, R. L.; Kahn, S. D.; Hehre, W J. J. Am. Chem. Soc. 1987,109, 672-677.
37. (b) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860.
38. -1.
39. Peng, C.; Schlegel, H. B. Isr. J. Chem. 1993, 33, 449-454.