Enantioselective synthesis of α-hydroxyphosphonates through asymmetric Pudovik reactions with chiral lanthanoid and titanium alkoxides

Abstract

The Pudovik reaction of aromatic aldehydes with diethyl phosphite catalysed by either tartrate-modified titanium(IV) alkoxides or binaphthol-modified lanthanoid alkoxides has been examined. The enantioselectivity for the Pudovik reaction catalysed by tartrate-modified titanium(IV) alkoxide 1 was strongly dependent upon the solvent used. The electronic nature of the carbonyl affected the enantioselectivity for the Pudovik reaction with the La-Li-BINOL complex 2.

References

1. The Role of Phosphonates in Living Systems, R. K. Hilderbrand(ed.), CRC Press, Boca Raton, FL, 1983.
2. (a) D. V. Patel, K. Rielly-Gauvin and D. E. Ryono, Tetrahedron Lett., 1990, 31, 5587, 5591; (b) R. T. Wester, R. J. Chamber, M. D. Green and W. R. Murphy, Bioorg. Med. Chem. Lett., 1994, 4, 2005; (c) D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, C. A. Free, W. L. Rogers, S. A. Smithy, J. M. DeForrest, R. S. Oehle and E. W. Petrillo Jr., J. Med. Chem., 1995, 38, 4557.
3. B. Stowasser, K.-H. Budt, L. Jian-Qi, A. Peyman and D. Ruppert, Tetrahedron Lett., 1992, 33, 6625.
4. J. A. Sikorski, M. J. Miller, D. S. Braccolino, D. G. Cleary, S. D. Corey, J. L. Font, K. J. Gruys, C. Y. Han, K. C. Lin, P. D. Pansegrau, J. E. Ream, D. Schnur, A. Shah and M. C. Walker, Phosphorus, Sulfur, Silicon, Relat. Elem., 1993, 76, 115.
5. T. R. Burke Jr., Z.-H. Li, J. B. Bolen and V. E. Marquez, J. Med. Chem., 1991, 34, 1577.
6. (a) F. Hammerschmidt and H. Völlenkle, Liebigs Ann. Chem., 1989, 577; (b) T. Yokomatsu and S. Shibuya, Tetrahedron: Asymmetry, 1992, 3, 377; (c) T. Yokomatsu, Y. Yoshida and S. Shibuya, J. Org. Chem., 1994, 59, 7930; (d) T. Gajda, Tetrahedron: Asymmetry, 1994, 5, 1965; (e) T. Yokomatsu, K. Suemune, T. Yamagishi and S. Shibuya, Synlett, 1995, 847.
7. Reviews on stereoselective synthesis of α-amino phosphonic acids: (a) B. Dhawan and D. Redmore, Phosphorus Sulfur, Relat. Elem., 1987, 32, 119; (b) L. Maier, Phosphorus, Sulfur, Silicon, Relat. Elem., 1990, 53, 43; (c) Handbook of Organophosphorus chemistry, (ed.)R. Engel, Marcel Dekker, New York, 1992; (d) V. P. Kukhar', V. A. Soloshonok and V. A. Solodenko, Phosphorus, Sulfur, Silicon, Relat. Elem., 1994, 92, 239.
8. V. Sum and T. P. Kee, J. Chem. Soc., Perkin Trans. 1, 1993, 2701 and references cited therein.
9. Synthesis of Carbon-Phosphorus Bonds(ed.)R. Engel, CRC Press, Boca Raton, FL, 1987.
10. V. J. Blazis, K. J. Koeller and C. D. Spilling, J. Org. Chem., 1995, 60, 931 and references cited therein.
11. (a) H. Wynberg and A. A. Smaardijk, Tetrahedron Lett., 1983, 24, 5899; (b) A. A. Smaardijk, S. Noorda, F. van Bolhulis and H. Wynberg, Tetrahedron Lett., 1985, 26, 493.
12. (a) T. Yokomatsu, T. Yamagishi and S. Shibuya, Tetrahedron: Asymmetry, 1993, 4, 1779; (b) T. Yokomatsu, T. Yamagishi and S. Shibuya, Tetrahedron: Asymmetry, 1993, 4, 1783.
13. (a) N. P. Rath and C. D. Spilling, Tetrahedron Lett., 1994, 35, 227; (b) T. Arai, M. Bougauchi, H. Sasai and M. Shibasaki, J. Org. Chem., 1996, 61, 2926; (c) see also H. Sasai, S. Arai, Y. Tahara and M. Shibasaki, J. Org. Chem., 1995, 60, 6656 for asymmetric hydrophosphonylation of imines promoted by the La-K-BINOL complex.
14. (a) H. Sasai, T. Suzuki, N. Itoh and M. Shibasaki, Tetrahedron Lett., 1993, 34, 851; (b) H. Sasai, N. Itoh, T. Suzuki and M. Shibasaki, Tetrahedron Lett., 1993, 34, 855; (c) H. Sasai, T. Suzuki, N. Itoh, S. Arai and M. Shibasaki, Tetrahedron Lett., 1993, 34, 2657; (d) H. Sasai, T. Suzuki, N. Itoh, K. Tanaka, T. Date, K. Okamura and M. Shibasaki, J. Am. Chem. Soc., 1993, 115, 10372; (e) H. Sasai, T. Arai and M. Shibasaki, J. Am. Chem. Soc., 1994, 116, 1571; (f) H. Sasai, T. Arai, Y. Satow, K. N. Houk and M. Shibasaki, J. Am. Chem. Soc., 1995, 117, 6194 and references cited therein.
15. (a) M. G. Finn and K. B. Sharpless, Asymmetric Synthesis, ed. J. M. Morrison, Academic Press Inc., New York, vol. 5, pp. 247, 1985 and references cited therein; (b) M. Hayshi, T. Matsuda and N. Oguni, J. Chem. Soc., Chem. Commun., 1990, 1364.
16. (a) V. Gutmann, The Donor-Acceptor Approach to Molecular Interaction, Plenum Press, New York, 1978; (b) see also K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima and J. Sugimori, J. Am. Chem. Soc., 1989, 111, 5340.
17. M. L. Peterson, S. D. Corey, J. A. Sikorski and M. C. Walker, Abstracts of Paper, 203rd American Chemical Society National Meeting, San Francisco, 1992, ORGN 469.
18. K. Fukui, T. Yonezawa and C. Nagata, Bull. Chem. Soc. Jpn., 1954, 27, 423.
19. (a) F. Hammerschmidt and Y.-F. Li, Tetrahedron, 1994, 50, 10253; (b) see also J. K. Kozlowski, N. P. Rath and C. D. Spilling, Tetrahedron, 1995, 51, 6385.
20. (a) T. D. Smith, J. Inorg. Nucl. Chem., 1960, 15, 95; (b) K. Moedritzer, J. Inorg. Nucl. Chem., 1961, 22, 19; (c) see also ref.10.
21. T. Kusumi, T. Fukushima, I. Ohtani and H. Kakisawa, Tetrahedron Lett., 1991, 32, 2939.