Electrophilic amination of organozinc reagents with acetone O-(2,4,6-trimethylphenylsulfonyl)oxime and O-methylhydroxylamine

Abstract

Reaction of diorganozincs and triorganozincates with acetone O-(2,4,6-trimethylphenylsulfonyl)oxime or O-methylhydroxylamine in the presence of CuCN provides a new one-flask method for electrophilic amination of organozinc reagents. Considering the lithium- or magnesium-to-zinc transmetallation, this method also extends the scope of electrophilic amination of organolithiums and Grignard reagents.

References

1. (a) E. Erdik and M. Ay, Chem. Rev., 1989, 89, 1947; (b) J. Mulzer, H. J. Altenbach, M. Brown, K. Krohn and H. U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1991, p. 45; (c) R. Askani and D. F. Taber, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon Press, Oxford, 1996, vol. 7, p. 1881.
2. A. Casarini, P. Dembech, D. Lazzari, E. Marini, G. Reginato, A. Ricci and G. Seconi, J. Org. Chem., 1993, 58, 5620.
3. (a) J. P. Genêt, S. Mallart, C. Greck and E. Piveteau, Tetrahedron Lett., 1991, 32, 2359; (b) C. Greck, L. Bischo, A. Girard, J. Hajicek and J. P. Genêt, Bull. Soc. Chim. Fr., 1994, 131, 429; (c) C. Greck, L. Bischoff, F. Ferreira and J. P. Genêt, J. Org. Chem., 1995, 60, 7010; (d) J. P. Genêt and C. Greck, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, New York, 1995, vol. 1, p. 898; (e) N. Zheng, J. D. Armstrong, III, J. C. McWilliams and R. P. Volante, Tetrahedron Lett., 1997, 38, 2817.
4. (a) S. Andrea and E. Schmitz, Synthesis, 1991, 327; (b) J. Vidal, J. Drouin and A. Collet, J. Chem. Soc., Chem. Commun., 1991, 435; (c) D. A. Niederer, J. T. Kapron and J. C. Vederas, Tetrahedron Lett., 1993, 34, 6859; (d) J. Vidal, L. Guy, S. Sterlin and A. Collet, J. Org. Chem., 1993, 58, 4791; (e) J. Vidal, S. Damestoy and A. Collet, Tetrahedron Lett., 1995, 36, 1439.
5. (a) W. Oppolzer and O. Tamura, Tetrahedron Lett., 1990, 31, 991; (b) W. Oppolzer, O. Tamura, G. Sundarababu and M. Signer, J. Am. Chem. Soc., 1992, 114, 5900.
6. (a) E. Erdik and M. Ay, Synth. React. Inorg. Metal.-Org. Chem., 1989, 19, 663; (b) E. Erdik, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, New York, 1995, vol. 1, p. 41.
7. H. Tsutsui, J. Hayashi and K. Narasaka, Chem. Lett., 1997, 317.
8. H. Mitchell and J. Leblanc, J. Org. Chem., 1994, 59, 682.
9. P. Beak and G. W. Selling, J. Org. Chem., 1989, 54, 5574.
10. A. Alberti, F. Canè, P. Dembech, D. Lazzari, A. Ricci and G. Seconi, J. Org. Chem., 1996, 61, 1677.
11. B. Carboni and M. Voultier, Bull. Soc. Chim. Fr., 1995, 132, 1003.
12. R. Hagopian, M. J. Therien and J. R. Murdoch, J. Am. Chem. Soc., 1984, 106, 5753.
13. (a) G. H. Coleman, J. L. Hermanson and W. J. Johnson, J. Am. Chem. Soc., 1937, 59, 1896; (b) G. H. Coleman, W. P. Andersen and J. L. Hermanson, J. Am. Chem. Soc., 1934, 56, 1381.
14. C. Greck, L. Bischoff, F. Ferreira, C. Pinel, E. Piveteau and J. P. Genêt, Synlett, 1993, 475.
15. F. Canè, D. Brancaleoni, P. Dembech, A. Ricci and G. Seconi, Synthesis, 1997, 545.
16. R. Reike, Tetrahedron Lett., 1998, 39, 9157.
17. P. Knochel and R. Singer, Chem. Rev., 1993, 93, 2117.
18. P. Knochel, Synlett, 1995, 393.
19. E. Erdik, Organozinc Reagents in Organic Synthesis, CRC Press, Florida, 1996.
20. P. Knochel, J. J. Almena and P. Jones, Tetrahedron, 1998, 54, 8275.
21. P. Beak and B. J. Kokko, J. Org. Chem., 1982, 47, 2822.
22. R. Brown and W. Jones, J. Chem. Soc., 1946, 781.
23. N. I. Scheverdina and Z. Kotscheschkov, J. Gen. Chem. USSR (Engl. Transl.), 1938, 8, 1825.
24. E. Erdik and T. Daşkapan, Synth. Commun., 1999, 29 (in publication).
25. M. Uchiyama, M. Kemada, O. Mishima, N. Yokoyama, M. Koike, Y. Kondo and T. Sakamoto, J. Am. Chem. Soc., 1998, 120, 4934.
26. B. M. Trost and W. H. Pearson, J. Am. Chem. Soc., 1983, 105, 1054.
27. J. Leonard, B. Lygo and G. Procter, Advanced Practical Organic Chemistry, Blackie, London, 1995.
28. G. B. Kaufman and L. A. Teter, Inorg. Synth., 1963, 7, 9.
29. H. J. Barber, J. Chem. Soc., 1943, 1, 79.
30. R. J. K. Taylor, Organocopper Reagents. A Practical Approach, Oxford University Press, Oxford, 1994.
31. Y. Yamamato, Y. Chounan, M. Tanaka and T. Ibuka, J. Org. Chem., 1992, 57, 1024.
32. L. A. Carpino, J. Am. Chem. Soc., 1960, 82, 3133.
33. H. Hjeds, Acta Chem. Scand., 1965, 19, 1764.
34. J. C. Watson and J. F. Eastham, J. Organomet. Chem., 1967, 9, 165.
35. B. S. Furniss, A. J. Hannaford, V. Rogers, P. W. G. Smith and A. R. Tachell, Vogel's Textbook of Practical Organic Chemistry, Longman, London, 1981, p. 1129.
36. Handbook of Tables for Organic Compound Identification, ed. Zvi Rappoport, CRC Press, Inc., Florida, 1980.
37. The Aldrich Library of ¹³ C and ¹ H NMR Spectra, ed. C. J. Pouchert and J. Behnke, Aldrich Chem. Co., Milwaukee, 1993.