Diastereoselective addition of metal-coordinated and 'naked' nucleophilic reagents to norephedrine derived 2-acyl-N-tosyl-oxazolidines

Tetrahedron

Volumn 53, Issue 5, 1997, Pages 1759-1776

  Poli, Giovanni ^a   Maccagni, Elisa ^a   Manzoni, Leonardo ^b   Pilati, Tullio ^c   Scolastico, Carlo ^b  

^a CNR   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

^c Ctro per lo Stud delle R   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

NOREPHEDRINE; OXAZOLIDINE DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

EID: 0031550594     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01087-3     Document Type: Article

References (78)

1. 1. Leading references: (a) Greeves, N. in: Comprehensive Organic Synthesis, vol 8, ch. 1.1, Trost, B.M., Fleming, I., Eds; Pergamon: Oxford, U.K.,
2. (b) Huryn, D.M. in: Comprehensive Organic Synthesis, Trost, B.M., Fleming, I., Eds; Pergamon: Oxford, U.K., Vol 1, p 49.
3. (c) Wigfield, D.C. Tetrahedron, 1979, 35, 449.
4. (d) Reetz, M.T. Angew.Chem.Int.Ed.Engl. 1984, 23, 556.
5. (e) Lodge E.P.; Heathcock, C.H. J.Am.Chem.Soc., 1987, 109, 3353.
6. (f) Fraser, R.R.; Stanciulescu, M. J.Am.Chem.Soc., 1987, 109, 1580.
7. (g) Cieplak, A.S.; Tait, B.D.; Johnson, C.R. J.Am.Chem.Soc., 1989, 111, 8447.
8. (h) Kurita, Y.; Takayama, C. Tetrahedron, 1990, 46, 6633.
9. (i) Paquette, L.A.; Underiner, T.L.; Gallucci, G.C.; J.Org.Chem., 1992, 57, 86;
10. 2. Leading references: (a) Houk, K.N.; Wu, Y-D. Stereochemistry of Organic and Bioorganic Transformations, Bartmann, W.; Sharpless, K.B. Eds; VCH Publishers, New York 1987; p 247-260.
11. (b) Anh, N.T.; Eisenstein, O. Nouv.J.Chim., 1977, 1, 61.
12. (c) Anh, N.T.; Top.Curr.Chem. 1980, 88, 145.
13. (d) Cieplak, A.S. J.Am.Chem.Soc., 1981, 103, 4540.
14. (e) Mukherjee, D.; Wu, Y-D.; Fronkzek, F.R.; Houk, K.N. J.Am.Chem.Soc., 1988, 110, 3328; Wong, S.S.;
15. (f) Paddon-Row, M.N. J.Chem.Soc., Chem.Commun., 1990, 456;
16. (g) Wong, S.S.; Paddon-Row, M.N. J.Chem.Soc., Chem.Commun., 1991, 327;
17. (h) Wu, Y-D.; Tucker, J.A. Houk, K.N. J.Am.Chem.Soc. 1991, 113, 5018;
18. (i) Reetz, M.T. Acc.Chem.Res. 1993, 26, 462.
19. (k) Frenking, G.; Köhler, K.F.; Reetz, M.T. Tetrahedron, 1993, 49, 3983.
20. (l) Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J.Chem.Soc. Faraday Trans., 1994, 90, 1789.
21. (m) Mori, S.; Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J.Am.Chem.Soc., 1995, 117, 5055.
22. 3. See for example: (a) Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C; Villa, R. J.Org.Chem., 1988, 53, 1600;
23. (b) Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929.
24. (c) Belvisi, L.; Pasquarello, A.; Poli, G.; Scolastico, C. Synlett 1992, 93.
25. (d) Carugo, O.; Poli, G. J.Mol.Struct. 1994, 318, 189.
26. 4. Manzoni, L.; Pilati, T.; Poli, G.; Scolastico, C. J.Chem.Soc. Chem.Commun. 1992, 1027.
27. 5. Poli, G.; Maccagni, E.; Manzoni, L.; Pilati, T.; Scolastico, C. Synlett, 1995, 71.
28. 6. (a) Ukaji, Y.; Yamamoto, K.; Fukui, M.; Fujisawa, T. Tetrahedron Letters 1991 32, 2919.
29. (b) Bai, X.; Eliel, E.L. J.Org.Chem 1992, 57, 5166.
30. (c) Maglioli, P.; De Lucchi, O.; Delogu, G.; Valle, G. Tetrahedron: Asymmetry 1992, 3, 365.
31. (d) Frieboes, K.C.; Harder, T.; Aulbert, D,; Strahriger, C.; Bolte, M.; Hoppe, D. Synlett 1993, 921.
32. (e) Harder, T.; Löhl, T.; Bolte, M. Wagner, K.; Hoppe, D. Tetrahedron Letters, 1994, 35, 7365.
33. (f) Agami, C.; Couty, F.; Lequesne, C. Tetrahedron Letters 1994, 35, 3309.
34. (g) Colombo, L.; Di Giacomo M.; Brusotti, G.; Delogu, G. Tetrahedron Letters, 1994, 35, 2063.
35. (h) Colombo, L.; Di Giacomo, M.; Brusotti, G.; Milano, E. Tetrahedron Letters, 1995, 36, 2863.
36. (i) Agami, C.; Couty, F.; Lequense, C. Tetrahedron, 1995, 51, 4043.
37. 7. Cis selectivity in acid catalyzed oxazolidine cyclizations is well documented: Cardani, S.; Bernardi, A.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R., J.Org.Chem., 1988, 53, 1600.
38. 8. (a) Poli, G. Tetrahedron Lett., 1989, 31, 7385.
39. (b) See also: Colombo, L.; Gennari, C.; Poli, G.; Scolastico, C.; De Munari, S. Tetrahedron Lett., 1985, 26, 5459.
40. 9. (a) Redlich, H.; Schneider, B. Liebigs Ann. Chem., 1983, 412.
41. (b) Bernardi, A.; Poli, G.; Scolastico, C.; Zanda, M. J.Org.Chem., 1991, 56, 6961.
42. 10. See for example: (a) Curran, D.P.; Zhang, J. J.Chem.Soc. Perkin Trans 1, 1991, 2613.
43. (b) Akiyama, T.; Ozaki, S. Tetrahedron Letters 1991, 32, 1335.
44. (c) Akiyama, T.; Nishimoto, H.; Kuwata, T.; Ozaki, S. Bull.Chem.Soc.Jpn., 1994, 67, 180.
45. (d) Conole, G.; Mears, R.J.; Desilva, H.; Whiting, A. J.Chem.Soc. Perkin Trans. I, 1995, 1825.
46. (e) Ono, S.; Shuto, S.; Matsuda, A. Tetrahedron Letters, 1996, 37, 221.
47. 11. B. Dietrich, in: Inclusion Compounds, Atwood, J.L.; Davies, J.E.D.; McNicol, D.D. Eds., Academic Press, 1984, ch 10, pp. 392-393.
48. 12. (a) Pierre J.L.; Handel, H. Tetrahedron Letters, 1974, 15, 2317.;
49. (b) Loupy, A.; Seyden-Penne J.; Tchoubar, B. Tetrahedron Letters, 1976, 17, 1677.
50. 13. (a) Ko, K-J.; Frazee, W.J.; Eliel, E.L. Tetrahedron, 1984, 40, 1333.
51. see also: (b) Frye S.V.; Eliel, E.L.; J.Am.-Chem.Soc., 1988, 110, 484.
52. 14. Eis, M.J.; Wrobel, J.E.; Ganem, B., J.Am.Chem.Soc., 1984, 106, 3693
53. 15. For similar reversals of diastereoselection between organolithium and grignard reagents in carbonyl additions see for example: (a) ref. 6c;
54. (b) Wade, P.A.; Price, D.T.; McCauley, J.P., J.Org.Chem., 1985, 50, 2804.
55. 16. Yamataka, H.; Miyano, N.; Hanafusa, T., J.Org.Chem., 1991, 56, 2573.
56. 17. (a) Chen, X.; Hortelano, E.R.; Eliel, E.L.; Frye, S.V. J.Am.Chem.Soc., 1992, 114, 1778;
57. (b) Chen, X.; Hortelano, E.R.; Eliel, E.L. J.Am.Chem.Soc., 1990, 112, 6130.
58. 18. Chelation between bicoordinating Lewis acids and carbonyl oxygens is well documented: (a) ref 1d.
59. (b) Shambayati, S.; Schreiber, S.L. in: Comprehensive Organic Synthesis Comprehensive Organic Synthesis, vol 1, ch. 10, Trost, B.M., Fleming, I., Eds. Pergamon: Oxford, U.K. On the other hand, only a few known precedents involve sulfonamides:
60. (c) Oppolzer, W.; Rodriguez, I.; Blagg, J.; Bernardinelli, G. Helv.Chim.Acta., 1989, 72, 123.
61. (d) Oppolzer, W.; Poli, G.; Kingma, A.J.; Starkemann, C.; Bernardinelli, G. Helv.Chim.Acta, 1987, 70, 2201.
62. 19. Theoretical studies predict transition states with rather obtuse angles of attack in the absence of electrophilic activation. Houk, K.N.; Paddon-Row, M.N.; Rondan, N.G.; Wu, J-D.; Brown, F.K.; Spellmeyer, D.C.; Metz, J.T.; Li, Y.; Loncharich, R.J. Science, 1986, 231, 1108.
63. 20. Spartan V3.1, Wavefunction, Inc.
64. 21. Stewart, J.P. J.Computer-Aided Mol.Des., 1990, 4, 3.
65. 22. The atomic charges where obtained from fit to the electrostatic potential.
66. 23. The algebraic sum of the charges relative to all the atoms constituting the mesyl moiety was considered.
67. 3 electron isodensity surface gave maximum absolute values of 0.04788 and 0.04665 respectively, both located on the π-carbonyl Re faces.
68. 25. Further theoretical work at the transition state level is planned in order to obtain more information on this stereochemical model.
69. 26. Such an experiment is expected to reflect a time-averaged dynamic equilibrium resulting from the fast exchange between magnesium ion and all the Lewis basic sites (i.e. the oxygen atoms of the carbonyl, the sulfone, the oxazolidine ring, and ethyl ether).
70. 27. Precedents of intramolecular SO - HO chelation are known. See for example: (a) Pyne, S.G.; Bloem, P.; Griffith, R. Tetrahedron, 1989, 45, 7013.
71. (b) Delogu, G.; De Lucchi, O.; Maglioli, P. Synlett, 1989, 28.
72. (c) Bernardi, A.; Colombo, L.; Gennari, C.; Prati, L. Tetrahedron, 1984, 40, 3775.
73. 28. Hasnoot, C.A.; DeLeeuw, F.A.; Altona, C. Tetrahedron, 1980, 36, 2783.
74. 29. Bernardi, A; Piarulli, U.; Scolastico, C.; Villa, R. Bull.Soc.Chim.Fr. 1990, 127, 751.
75. 30. Crassland, I. Org. Synth. 1981, 60, 6.
76. 31. Main, P.; Fiske, S.; Hull, S.; Lessinger, L.; Germain, G.; Declerq, J.P.; Woolfson, M.M. A System of Computer Programs for the Automatic Solution of Crystal Structure from X-ray Diffraction Data, Universities of York, England and Louvain, Belgium, 1980.
77. 32. Frenz, B.A. Enraf-Nonius Structures Determination Package; SDP Users Guide, 1983, Enraf-Nonius, Delft, The Netherlands.
78. 33. Bianchi, A.; Gramaccioli, C.M.; Pilati, T.; Simonetta, M. Acta Cryst., 1981, A37, 65.