Titanium chelation in regioselective Michael additions to conjugated dienones and trienones

Tetrahedron Letters

Volumn 38, Issue 36, 1997, Pages 6319-6322

  Brocchini, Stephen J ^a   Lawton, Richard G ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; KETONE; POLYENE; THIOL DERIVATIVE;

ARTICLE; CATALYSIS; CHELATION; COMPLEX FORMATION; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 0030765943     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01452-4     Document Type: Article

References (27)

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2. 13C-NMR(acetone-d6) δ 188.5, 149.5, 146.3, 140.0, 136.4, 134.9, 131.2, 128.0, 127.8, 126.3, 123.6.
3. 3) δ 2.48(s, 1 H), 2.64(t, 2 H), 3.15(d, 2 H), 3.68(t, 2 H), 3.81(d, 2 H), 5.57-5.69(ddd(qu), 1 H), 5.62-5.72(ddd(qu), 1 H), 7.68(t, 1 H), 8.25(d, 1 H), 8.39(d, 1 H), 8.70(s, 1 H).
4. 3) δ 2.63-2.78(m, 2 H), 3.33(ddd, 2 H), 3.75( t, 2 H), 3.93(ddd as a q, 1 H), 5.13(dd as a t, 2 H), 5.68-5.78(ddd, 1 H), 7.68(t, 1 H, J=8.14Hz), 8.26(d 1 H, J=6.98Hz), 8.40(d, 1 H), 8.73(s, 1 H). All proton relationships identified through COSEY and NOSEY NMR study.
5. Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211-5212.
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10. Liberatore, F. A.; Comeau, R. D.; McKearin, J. M.; Pearson, D. A.; Belonga, B. Q.; Brocchini, S. J.; Kath, J.; Phillips, T.; Oswell, K.; Lawton, R. G. Bioconjugate Chem. 1990, 1, 36; del Rosario, R. B.; Brocchini, S. J.; Lawton, R. G.; Wahl, R. L.; Smith, R. Bioconjugate Chemistry 1990, 1, 50; del Rosario R.; Brocchini, S.J.; Baron, L.A.; Lawton, R.G.; Smith, R.H.; Jackson G.A.; Scott, P.A.; Clavo, A.C.; Fischer, S. J.; Wahl, R.L. J. Nucl. Med. 1989, 30, 832. del Rosario R.; Brocchini, S.J.; Baron, L.A.; Lawton, R.G.; Smith, R.H.; Jackson, G.A.; Scott, P.A.; Clavo, A.C.; Fischer, S. J.; Wahl, R.L. (1989), 4th International Conference on Monoclonal Antibody Immunoconjugates for Cancer, March 1989, San Diego, CA.
11. Liberatore, F. A.; Comeau, R. D.; McKearin, J. M.; Pearson, D. A.; Belonga, B. Q.; Brocchini, S. J.; Kath, J.; Phillips, T.; Oswell, K.; Lawton, R. G. Bioconjugate Chem. 1990, 1, 36; del Rosario, R. B.; Brocchini, S. J.; Lawton, R. G.; Wahl, R. L.; Smith, R. Bioconjugate Chemistry 1990, 1, 50; del Rosario R.; Brocchini, S.J.; Baron, L.A.; Lawton, R.G.; Smith, R.H.; Jackson G.A.; Scott, P.A.; Clavo, A.C.; Fischer, S. J.; Wahl, R.L. J. Nucl. Med. 1989, 30, 832. del Rosario R.; Brocchini, S.J.; Baron, L.A.; Lawton, R.G.; Smith, R.H.; Jackson, G.A.; Scott, P.A.; Clavo, A.C.; Fischer, S. J.; Wahl, R.L. (1989), 4th International Conference on Monoclonal Antibody Immunoconjugates for Cancer, March 1989, San Diego, CA.
12. Liberatore, F. A.; Comeau, R. D.; McKearin, J. M.; Pearson, D. A.; Belonga, B. Q.; Brocchini, S. J.; Kath, J.; Phillips, T.; Oswell, K.; Lawton, R. G. Bioconjugate Chem. 1990, 1, 36; del Rosario, R. B.; Brocchini, S. J.; Lawton, R. G.; Wahl, R. L.; Smith, R. Bioconjugate Chemistry 1990, 1, 50; del Rosario R.; Brocchini, S.J.; Baron, L.A.; Lawton, R.G.; Smith, R.H.; Jackson G.A.; Scott, P.A.; Clavo, A.C.; Fischer, S. J.; Wahl, R.L. J. Nucl. Med. 1989, 30, 832. del Rosario R.; Brocchini, S.J.; Baron, L.A.; Lawton, R.G.; Smith, R.H.; Jackson, G.A.; Scott, P.A.; Clavo, A.C.; Fischer, S. J.; Wahl, R.L. (1989), 4th International Conference on Monoclonal Antibody Immunoconjugates for Cancer, March 1989, San Diego, CA.
13. Liberatore, F. A.; Comeau, R. D.; McKearin, J. M.; Pearson, D. A.; Belonga, B. Q.; Brocchini, S. J.; Kath, J.; Phillips, T.; Oswell, K.; Lawton, R. G. Bioconjugate Chem. 1990, 1, 36; del Rosario, R. B.; Brocchini, S. J.; Lawton, R. G.; Wahl, R. L.; Smith, R. Bioconjugate Chemistry 1990, 1, 50; del Rosario R.; Brocchini, S.J.; Baron, L.A.; Lawton, R.G.; Smith, R.H.; Jackson G.A.; Scott, P.A.; Clavo, A.C.; Fischer, S. J.; Wahl, R.L. J. Nucl. Med. 1989, 30, 832. del Rosario R.; Brocchini, S.J.; Baron, L.A.; Lawton, R.G.; Smith, R.H.; Jackson, G.A.; Scott, P.A.; Clavo, A.C.; Fischer, S. J.; Wahl, R.L. (1989), 4th International Conference on Monoclonal Antibody Immunoconjugates for Cancer, March 1989, San Diego, CA.
14. 13C-NMR(acetone-d6) δ 188.2, 149.5, 146.0, 144.0, 140.3, 137.5, 134.8, 132.1, 131.2, 127.7, 125.7, 123.5, 122.8.
15. 3) δ 2.71(t, 2H), 3.2(d, 2H), 3.70(t, 2H), 3.82(d, 2H), 5.68(m, 2H), 6.05(q, 1H), 6.32(q, 1H), 7.65(t, 1H), 8.22(d, 1H), 8.44(d, 1H), 8.75(s, 1H).
16. 3) δ 2.75(m, 2H), 3.38(t, 2H), 3.80(t, 2H), 4.96(q, 1H), 5.63(m, 1H) imposed on 5.66(d, 1H), 5.90(m, 1H), 6.10(m, 1H), 6.33(m, 1H), 7.65(t, 1H), 8.22(d, 1H), 8.42(d, 1H), 8.78(s, 1H).
17. Lehnert, W. Tetrahedron Lett. 1970, 4723.
18. Harrison, C. R. Tetrahedron Lett. 1987, 1435.
19. 3) δ 1.94 (d, 3H), 2.14(t, 1H), 2.68(t, 2H) 3.28(d, 2H), 3.75(q, 2H) 5.94(q, 1H), 6.14(sex, 1H) 6.40-6.68(m, 3H), 7.65(t, 1H), 8.09(d, 1H), 8.39(d, 1H), 8.53(s, 1H). Sulfone by mCPBA oxidation, mp 109-115°C.
20. Posner, T. Chem. Ber. 1902, 35, 799 ; Chem. Ber. 1904, 37, 502.
21. Posner, T. Chem. Ber. 1902, 35, 799 ; Chem. Ber. 1904, 37, 502.
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23. 13C-NMR(acetone-d6) δ 187.9, 148.4, 146.6, 143.5, 139.5, 135.8, 133.9, 129.9, 129.6, 128.9, 127.5, 126.9, 126.5, 123.9, 123.2.
24. 13C-NMR(acetone-d6) δ 196.1, 148.5, 137.9, 133.5, 129.9, 129.4, 128.7, 128.6, 128.1, 127.8, 127.4, 126.4, 122.8, 61.0, 43.4, 42.8, 31.1.
25. Evans, D. A.; Urpi, F.; Somers, T.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215 and subsequent papers.
26. Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, U. T.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 867.
27. Yura, T.; Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1986, 187.