Total Enantiotopic Discrimination between Carbon Atoms of a Double Bond in the Reaction of Diolates with meso-Bis(phenylsulfonyl)alkenes - Synthesis of Enantiopure Ketones

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 13-14, 1997, Pages 1504-1506

  Cossu, Sergio ^a   De Lucchi, Ottorino ^a   Pasetto, Paolo ^a  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

Asymmetric synthesis; Chirality; Ketones; Synthetic methods

Indexed keywords

EID: 0030828246     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199715041     Document Type: Article

References (38)

1. E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, pp. 962-963.
2. E. Schoffers, A. Golebiowski, C. R. Johnson, Tetrahedron 1996, 52, 3769-3826; L. A. Paquette, H.-C. Tsui, J. Org. Chem. 1996, 61, 142-145.
3. E. Schoffers, A. Golebiowski, C. R. Johnson, Tetrahedron 1996, 52, 3769-3826; L. A. Paquette, H.-C. Tsui, J. Org. Chem. 1996, 61, 142-145.
4. N. S. Simpkins in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 111-125; D. M. Hodgson, A. R. Gibbs, G. P. Lee, Tetrahedron 1996, 52, 14361-14384.
5. N. S. Simpkins in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 111-125; D. M. Hodgson, A. R. Gibbs, G. P. Lee, Tetrahedron 1996, 52, 14361-14384.
6. Hydroboration: K, Burgess, W. A. van der Donk in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 181-211; hydrosilylation: E. Campi, P. Perlmutter, ibid., pp. 212-221.
7. Hydroboration: K, Burgess, W. A. van der Donk in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 181-211; hydrosilylation: E. Campi, P. Perlmutter, ibid., pp. 212-221.
8. O. De Lucchi, W. Adam in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, 1991, pp. 193-214.
9. G. Helmchen, A. Krotz, H.-P. Neumann, M. L. Ziegler, Liebigs Ann. Chem. 1993, 1313-1317.
10. M. Hono in Anticancer Agents Based on Natural Product Models, Academic Press, London, 1980, p. 73.
11. C. A. Flechter, H. Hilper, P. L. Myers, S. M. Roberts, R. J. Storer, J. Chem. Soc. Chem. Commun. 1989, 1707-1709.
12. L. Pasquato, O. De Lucchi, L. Krotz, Tetrahedron Lett. 1991, 32, 2177-2178.
13. S. Cossu, O. De Lucchi, Gazz. Chim. It. 1990, 120, 569-576.
14. T. Cohen, R. H. Ritter, D. Ouelette, J. Am. Chem. Soc. 1982, 104, 7142-7148; O. De Lucchi, G. Marchioro, Phosphorus Sulfur Relat. Elem. 1985, 24, 305-309; H. Landen, H.-D. Martin, A. Steigel, Chem. Ber: 1987, 120, 171-175; K. A. Herbert, M. G. Banwell, Synth. Commun. 1989, 19, 327-337; S. Cossu, O. De Lucchi, D. Fabbri, G. Licini. L. Pasquato, Org. Prep. Proc. Int. 1991, 23, 573-592; G. O'Doherty, R. D. Rogers, L. A. Paquette, J. Am. Chem. Soc. 1994, 116, 10883-10894.
15. T. Cohen, R. H. Ritter, D. Ouelette, J. Am. Chem. Soc. 1982, 104, 7142-7148; O. De Lucchi, G. Marchioro, Phosphorus Sulfur Relat. Elem. 1985, 24, 305-309; H. Landen, H.-D. Martin, A. Steigel, Chem. Ber: 1987, 120, 171-175; K. A. Herbert, M. G. Banwell, Synth. Commun. 1989, 19, 327-337; S. Cossu, O. De Lucchi, D. Fabbri, G. Licini. L. Pasquato, Org. Prep. Proc. Int. 1991, 23, 573-592; G. O'Doherty, R. D. Rogers, L. A. Paquette, J. Am. Chem. Soc. 1994, 116, 10883-10894.
16. T. Cohen, R. H. Ritter, D. Ouelette, J. Am. Chem. Soc. 1982, 104, 7142-7148; O. De Lucchi, G. Marchioro, Phosphorus Sulfur Relat. Elem. 1985, 24, 305-309; H. Landen, H.-D. Martin, A. Steigel, Chem. Ber: 1987, 120, 171-175; K. A. Herbert, M. G. Banwell, Synth. Commun. 1989, 19, 327-337; S. Cossu, O. De Lucchi, D. Fabbri, G. Licini. L. Pasquato, Org. Prep. Proc. Int. 1991, 23, 573-592; G. O'Doherty, R. D. Rogers, L. A. Paquette, J. Am. Chem. Soc. 1994, 116, 10883-10894.
17. T. Cohen, R. H. Ritter, D. Ouelette, J. Am. Chem. Soc. 1982, 104, 7142-7148; O. De Lucchi, G. Marchioro, Phosphorus Sulfur Relat. Elem. 1985, 24, 305-309; H. Landen, H.-D. Martin, A. Steigel, Chem. Ber: 1987, 120, 171-175; K. A. Herbert, M. G. Banwell, Synth. Commun. 1989, 19, 327-337; S. Cossu, O. De Lucchi, D. Fabbri, G. Licini. L. Pasquato, Org. Prep. Proc. Int. 1991, 23, 573-592; G. O'Doherty, R. D. Rogers, L. A. Paquette, J. Am. Chem. Soc. 1994, 116, 10883-10894.
18. T. Cohen, R. H. Ritter, D. Ouelette, J. Am. Chem. Soc. 1982, 104, 7142-7148; O. De Lucchi, G. Marchioro, Phosphorus Sulfur Relat. Elem. 1985, 24, 305-309; H. Landen, H.-D. Martin, A. Steigel, Chem. Ber: 1987, 120, 171-175; K. A. Herbert, M. G. Banwell, Synth. Commun. 1989, 19, 327-337; S. Cossu, O. De Lucchi, D. Fabbri, G. Licini. L. Pasquato, Org. Prep. Proc. Int. 1991, 23, 573-592; G. O'Doherty, R. D. Rogers, L. A. Paquette, J. Am. Chem. Soc. 1994, 116, 10883-10894.
19. T. Cohen, R. H. Ritter, D. Ouelette, J. Am. Chem. Soc. 1982, 104, 7142-7148; O. De Lucchi, G. Marchioro, Phosphorus Sulfur Relat. Elem. 1985, 24, 305-309; H. Landen, H.-D. Martin, A. Steigel, Chem. Ber: 1987, 120, 171-175; K. A. Herbert, M. G. Banwell, Synth. Commun. 1989, 19, 327-337; S. Cossu, O. De Lucchi, D. Fabbri, G. Licini. L. Pasquato, Org. Prep. Proc. Int. 1991, 23, 573-592; G. O'Doherty, R. D. Rogers, L. A. Paquette, J. Am. Chem. Soc. 1994, 116, 10883-10894.
20. Preliminary experiments on several other polycyclic bis(phenylsulfonyl)-alkenes [10] show that the reaction is general.
21. The X-ray structure analyses were carried out by Dr. Giovanni Valle (C. N. R., Centre Studi Biopolimeri, via Marzolo 1, 1-35131 Padova, Italy).
22. J. Spanget-Larsen, R. Gleiter, Tetrahedron 1983, 39, 3345-3350, and references therein.
23. E. Müller, Chem. Ber. 1976, 109, 3793-3803; U. Azzena, S. Cossu, O. De Lucchi, G. Melloni, Gazz. Chim. It. 1989, 119, 357-358.
24. E. Müller, Chem. Ber. 1976, 109, 3793-3803; U. Azzena, S. Cossu, O. De Lucchi, G. Melloni, Gazz. Chim. It. 1989, 119, 357-358.
25. Enantiopure 13: J. Martynow, M. Dimitroff, A. G. Fallis, Tetrahedron Lett. 1993, 34, 8201-8204, see also ref. [6]; enantiopure 14: M. Demuth, S. Chandrasekhar, K. Schaffner J. Am. Chem. Soc. 1984, 106, 1092-1095; D. A. Lightner, J. K. Gawronski, T. D. Bouman, ibid. 1980, 102, 5749-5754; 15: +388.0 (c 3.2, in pentane).
26. Enantiopure 13: J. Martynow, M. Dimitroff, A. G. Fallis, Tetrahedron Lett. 1993, 34, 8201-8204, see also ref. [6]; enantiopure 14: M. Demuth, S. Chandrasekhar, K. Schaffner J. Am. Chem. Soc. 1984, 106, 1092-1095; D. A. Lightner, J. K. Gawronski, T. D. Bouman, ibid. 1980, 102, 5749-5754; 15: +388.0 (c 3.2, in pentane).
27. Enantiopure 13: J. Martynow, M. Dimitroff, A. G. Fallis, Tetrahedron Lett. 1993, 34, 8201-8204, see also ref. [6]; enantiopure 14: M. Demuth, S. Chandrasekhar, K. Schaffner J. Am. Chem. Soc. 1984, 106, 1092-1095; D. A. Lightner, J. K. Gawronski, T. D. Bouman, ibid. 1980, 102, 5749-5754; 15: +388.0 (c 3.2, in pentane).
28. B. M. Trost, N. R. Schmuff, J. Am. Chem. Soc. 1985, 107, 396-405.
29. N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon, Oxford, 1993, pp. 334-372; B. M. Trost, H. C. Arndt, P. E. Strege, T. R. Verhoeven, Tetrahedron Lett. 1976, 3477-3480;
30. N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon, Oxford, 1993, pp. 334-372; B. M. Trost, H. C. Arndt, P. E. Strege, T. R. Verhoeven, Tetrahedron Lett. 1976, 3477-3480;
31. H. Künzer, M. Stahnke, G. Sauer, R. Wiechert, ibid. 1991, 32, 1949-1952; G. H. Lee, E. B. Choi, E. Lee, C. S. Pak, ibid. 1993, 34, 4541-4544; E. Alonso, D. Guijarro, M. Yus, Tetrahedron 1995, 51, 2699-2708; R. Giovannini, M. Petrini, Synlett 1995, 973-974.
32. H. Künzer, M. Stahnke, G. Sauer, R. Wiechert, ibid. 1991, 32, 1949-1952; G. H. Lee, E. B. Choi, E. Lee, C. S. Pak, ibid. 1993, 34, 4541-4544; E. Alonso, D. Guijarro, M. Yus, Tetrahedron 1995, 51, 2699-2708; R. Giovannini, M. Petrini, Synlett 1995, 973-974.
33. H. Künzer, M. Stahnke, G. Sauer, R. Wiechert, ibid. 1991, 32, 1949-1952; G. H. Lee, E. B. Choi, E. Lee, C. S. Pak, ibid. 1993, 34, 4541-4544; E. Alonso, D. Guijarro, M. Yus, Tetrahedron 1995, 51, 2699-2708; R. Giovannini, M. Petrini, Synlett 1995, 973-974.
34. H. Künzer, M. Stahnke, G. Sauer, R. Wiechert, ibid. 1991, 32, 1949-1952; G. H. Lee, E. B. Choi, E. Lee, C. S. Pak, ibid. 1993, 34, 4541-4544; E. Alonso, D. Guijarro, M. Yus, Tetrahedron 1995, 51, 2699-2708; R. Giovannini, M. Petrini, Synlett 1995, 973-974.
35. R. A. Holton, D. J. Grouse, A. D. Williams, R. M. Kennedy, J. Org. Chem. 1987, 52, 2317-2318; M. Fujii, K. Nakamura, H. Mekata, S. Oka, A. Ohno, Bull. Chem. Soc. Jpn. 1988, 61, 495-500; A. B. Smith III, K. J. Hale, J. P. McCauley, Jr., Tetrahedron Lett. 1989, 30, 5579-5582; A. R. Harris, T. J. Mason, G. R. Hannah, J. Chem. Res. Synop. 1990, 7, 218-219.
36. R. A. Holton, D. J. Grouse, A. D. Williams, R. M. Kennedy, J. Org. Chem. 1987, 52, 2317-2318; M. Fujii, K. Nakamura, H. Mekata, S. Oka, A. Ohno, Bull. Chem. Soc. Jpn. 1988, 61, 495-500; A. B. Smith III, K. J. Hale, J. P. McCauley, Jr., Tetrahedron Lett. 1989, 30, 5579-5582; A. R. Harris, T. J. Mason, G. R. Hannah, J. Chem. Res. Synop. 1990, 7, 218-219.
37. R. A. Holton, D. J. Grouse, A. D. Williams, R. M. Kennedy, J. Org. Chem. 1987, 52, 2317-2318; M. Fujii, K. Nakamura, H. Mekata, S. Oka, A. Ohno, Bull. Chem. Soc. Jpn. 1988, 61, 495-500; A. B. Smith III, K. J. Hale, J. P. McCauley, Jr., Tetrahedron Lett. 1989, 30, 5579-5582; A. R. Harris, T. J. Mason, G. R. Hannah, J. Chem. Res. Synop. 1990, 7, 218-219.
38. R. A. Holton, D. J. Grouse, A. D. Williams, R. M. Kennedy, J. Org. Chem. 1987, 52, 2317-2318; M. Fujii, K. Nakamura, H. Mekata, S. Oka, A. Ohno, Bull. Chem. Soc. Jpn. 1988, 61, 495-500; A. B. Smith III, K. J. Hale, J. P. McCauley, Jr., Tetrahedron Lett. 1989, 30, 5579-5582; A. R. Harris, T. J. Mason, G. R. Hannah, J. Chem. Res. Synop. 1990, 7, 218-219.