Remote 1,5-induction and steric approach control in Horner-Wadsworth-Emmons reactions. The stereoselective construction of trisubstituted, exocyclic double bonds from unsymmetric cyclic ketones

Chemical Communications

Volumn , Issue 23, 1996, Pages 2637-2638

  Lampe, Thomas F J ^a   Hoffmann, H M R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009181593     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960002637     Document Type: Article

References (23)

1. For reviews concerning Wittig and related reactions, see J. Clayton and S. Warren, Angew. Chem., Int. Ed. Engl., 1996, 35, 241; M. Schlosser, Top. Stereochem., 1970, 5, 1; J. Boutagy and R. Thomas, Chem. Rev., 1974, 74, 87; B. E. Maryanoff and A. B. Reitz, Chem. Rev., 1989, 89, 863.
2. For reviews concerning Wittig and related reactions, see J. Clayton and S. Warren, Angew. Chem., Int. Ed. Engl., 1996, 35, 241; M. Schlosser, Top. Stereochem., 1970, 5, 1; J. Boutagy and R. Thomas, Chem. Rev., 1974, 74, 87; B. E. Maryanoff and A. B. Reitz, Chem. Rev., 1989, 89, 863.
3. For reviews concerning Wittig and related reactions, see J. Clayton and S. Warren, Angew. Chem., Int. Ed. Engl., 1996, 35, 241; M. Schlosser, Top. Stereochem., 1970, 5, 1; J. Boutagy and R. Thomas, Chem. Rev., 1974, 74, 87; B. E. Maryanoff and A. B. Reitz, Chem. Rev., 1989, 89, 863.
4. For reviews concerning Wittig and related reactions, see J. Clayton and S. Warren, Angew. Chem., Int. Ed. Engl., 1996, 35, 241; M. Schlosser, Top. Stereochem., 1970, 5, 1; J. Boutagy and R. Thomas, Chem. Rev., 1974, 74, 87; B. E. Maryanoff and A. B. Reitz, Chem. Rev., 1989, 89, 863.
5. A. Abiko and S. Masamune, Tetrahedron Lett., 1996, 37, 1077; J. Mulzer, T. Speck, J. Buschmann and P. Luger, Tetrahedron Lett., 1995, 36, 7643; M. Suarez and G. B. Schuster, J. Am. Chem. Soc., 1995, 117, 6732; T. Furuta and M. Iwamura, J. Chem. Soc., Chem. Commun., 1994, 2167; S. E. Denmark and C.-T. Chen, J. Am. Chem. Soc., 1992, 114, 10674; S. Hanessian and S. Beaudoin, Tetrahedron Lett., 1992, 33, 7659.
6. A. Abiko and S. Masamune, Tetrahedron Lett., 1996, 37, 1077; J. Mulzer, T. Speck, J. Buschmann and P. Luger, Tetrahedron Lett., 1995, 36, 7643; M. Suarez and G. B. Schuster, J. Am. Chem. Soc., 1995, 117, 6732; T. Furuta and M. Iwamura, J. Chem. Soc., Chem. Commun., 1994, 2167; S. E. Denmark and C.-T. Chen, J. Am. Chem. Soc., 1992, 114, 10674; S. Hanessian and S. Beaudoin, Tetrahedron Lett., 1992, 33, 7659.
7. A. Abiko and S. Masamune, Tetrahedron Lett., 1996, 37, 1077; J. Mulzer, T. Speck, J. Buschmann and P. Luger, Tetrahedron Lett., 1995, 36, 7643; M. Suarez and G. B. Schuster, J. Am. Chem. Soc., 1995, 117, 6732; T. Furuta and M. Iwamura, J. Chem. Soc., Chem. Commun., 1994, 2167; S. E. Denmark and C.-T. Chen, J. Am. Chem. Soc., 1992, 114, 10674; S. Hanessian and S. Beaudoin, Tetrahedron Lett., 1992, 33, 7659.
8. A. Abiko and S. Masamune, Tetrahedron Lett., 1996, 37, 1077; J. Mulzer, T. Speck, J. Buschmann and P. Luger, Tetrahedron Lett., 1995, 36, 7643; M. Suarez and G. B. Schuster, J. Am. Chem. Soc., 1995, 117, 6732; T. Furuta and M. Iwamura, J. Chem. Soc., Chem. Commun., 1994, 2167; S. E. Denmark and C.-T. Chen, J. Am. Chem. Soc., 1992, 114, 10674; S. Hanessian and S. Beaudoin, Tetrahedron Lett., 1992, 33, 7659.
9. A. Abiko and S. Masamune, Tetrahedron Lett., 1996, 37, 1077; J. Mulzer, T. Speck, J. Buschmann and P. Luger, Tetrahedron Lett., 1995, 36, 7643; M. Suarez and G. B. Schuster, J. Am. Chem. Soc., 1995, 117, 6732; T. Furuta and M. Iwamura, J. Chem. Soc., Chem. Commun., 1994, 2167; S. E. Denmark and C.-T. Chen, J. Am. Chem. Soc., 1992, 114, 10674; S. Hanessian and S. Beaudoin, Tetrahedron Lett., 1992, 33, 7659.
10. A. Abiko and S. Masamune, Tetrahedron Lett., 1996, 37, 1077; J. Mulzer, T. Speck, J. Buschmann and P. Luger, Tetrahedron Lett., 1995, 36, 7643; M. Suarez and G. B. Schuster, J. Am. Chem. Soc., 1995, 117, 6732; T. Furuta and M. Iwamura, J. Chem. Soc., Chem. Commun., 1994, 2167; S. E. Denmark and C.-T. Chen, J. Am. Chem. Soc., 1992, 114, 10674; S. Hanessian and S. Beaudoin, Tetrahedron Lett., 1992, 33, 7659.
11. T. F. J. Lampe, H. M. R. Hoffmann and U. T. Bornscheuer, Tetrahedron: Asymmetry, 1996, 7, 2889.
12. T. F. J. Lampe and H. M. R. Hoffmann, Tetrahedron Lett., 1996, 37, 7695; Chem. Commun., 1996, 1931.
13. T. F. J. Lampe and H. M. R. Hoffmann, Tetrahedron Lett., 1996, 37, 7695; Chem. Commun., 1996, 1931.
14. D. A. Evans and E. M. Carreira, Tetrahedron Lett., 1990, 31, 4703.
15. Chiral phosphonoacetates have been employed for controlling E/Z-selectivity in the synthesis of the prostacyclin analogue cicaprost; H.-J. Gais, G. Schmiedl, W. A. Ball, J. Bund, G. Hellmann and I. Erdelmeier, Tetrahedron Lett., 1988, 29, 1773; H. Rehwinkel, J. Skupsch and H. Vorbrüggen, Tetrahedron Lett., 1988, 29, 1775.
16. Chiral phosphonoacetates have been employed for controlling E/Z-selectivity in the synthesis of the prostacyclin analogue cicaprost; H.-J. Gais, G. Schmiedl, W. A. Ball, J. Bund, G. Hellmann and I. Erdelmeier, Tetrahedron Lett., 1988, 29, 1773; H. Rehwinkel, J. Skupsch and H. Vorbrüggen, Tetrahedron Lett., 1988, 29, 1775.
17. 3) along alternative chain segments in 4 (R = H). For 1,n-induction in the olefination of cyclic ketones, see (n = 2): E. G. Baggiolini, J. A. Iacobelli, B. M. Hennessy, A. D. Batcho, J. F. Sereno and M. R. Uskokovic, J. Org. Chem., 1986, 51, 3098; K. Tadano, Y. Idogaki, H. Yamada and T. Suami, J. Org. Chem., 1987, 52, 1201; J. Mulzer, U. Steffen, L. Zorn, C. Schneider, E. Weinhold, W. Münch, R. Rudert, P. Luger and H. Hartl, J. Am. Chem. Soc., 1988, 110, 4640; (n = 3): cf. ref. 6; (n = 4): K. Ohmori, T. Suzuki, K. Miyazawa, S. Nishiyama and S. Yamamura, Tetrahedron Lett., 1993, 34, 4981.
18. 3) along alternative chain segments in 4 (R = H). For 1,n-induction in the olefination of cyclic ketones, see (n = 2): E. G. Baggiolini, J. A. Iacobelli, B. M. Hennessy, A. D. Batcho, J. F. Sereno and M. R. Uskokovic, J. Org. Chem., 1986, 51, 3098; K. Tadano, Y. Idogaki, H. Yamada and T. Suami, J. Org. Chem., 1987, 52, 1201; J. Mulzer, U. Steffen, L. Zorn, C. Schneider, E. Weinhold, W. Münch, R. Rudert, P. Luger and H. Hartl, J. Am. Chem. Soc., 1988, 110, 4640; (n = 3): cf. ref. 6; (n = 4): K. Ohmori, T. Suzuki, K. Miyazawa, S. Nishiyama and S. Yamamura, Tetrahedron Lett., 1993, 34, 4981.
19. 3) along alternative chain segments in 4 (R = H). For 1,n-induction in the olefination of cyclic ketones, see (n = 2): E. G. Baggiolini, J. A. Iacobelli, B. M. Hennessy, A. D. Batcho, J. F. Sereno and M. R. Uskokovic, J. Org. Chem., 1986, 51, 3098; K. Tadano, Y. Idogaki, H. Yamada and T. Suami, J. Org. Chem., 1987, 52, 1201; J. Mulzer, U. Steffen, L. Zorn, C. Schneider, E. Weinhold, W. Münch, R. Rudert, P. Luger and H. Hartl, J. Am. Chem. Soc., 1988, 110, 4640; (n = 3): cf. ref. 6; (n = 4): K. Ohmori, T. Suzuki, K. Miyazawa, S. Nishiyama and S. Yamamura, Tetrahedron Lett., 1993, 34, 4981.
20. 3) along alternative chain segments in 4 (R = H). For 1,n-induction in the olefination of cyclic ketones, see (n = 2): E. G. Baggiolini, J. A. Iacobelli, B. M. Hennessy, A. D. Batcho, J. F. Sereno and M. R. Uskokovic, J. Org. Chem., 1986, 51, 3098; K. Tadano, Y. Idogaki, H. Yamada and T. Suami, J. Org. Chem., 1987, 52, 1201; J. Mulzer, U. Steffen, L. Zorn, C. Schneider, E. Weinhold, W. Münch, R. Rudert, P. Luger and H. Hartl, J. Am. Chem. Soc., 1988, 110, 4640; (n = 3): cf. ref. 6; (n = 4): K. Ohmori, T. Suzuki, K. Miyazawa, S. Nishiyama and S. Yamamura, Tetrahedron Lett., 1993, 34, 4981.
21. The synthesis of racemic ketones 3 and 4 is described in T. Lampe, PhD thesis, University of Hannover, 1996.
22. P. A. Wender, M. A. Eissenstat and M. P. Filosa, J. Am. Chem. Soc., 1979, 101, 2196.
23. In studies on the synthesis of monensin, a significant influence of phosphonates with different steric demands on the cis/trans ratio was observed; H. Nagaoka and Y. Kishi, Tetrahedron, 1981, 37, 3873 and ref. 7 therein.