Chemistry of Carbanions. XXIII. use of Metal Complexes to Control the Aldol Condensation

Journal of the American Chemical Society

Volumn 95, Issue 10, 1973, Pages 3310-3324

  House, Herbert O ^a   Crumrine, David S ^a   Teranishi, Allan Y ^a   Olmstead, Hugh D ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947085164     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00791a039     Document Type: Article

References (75)

1. H. O. House, “Modern Synthetic Reactions,” 2nd ed, W. A. Benjamin, Reading, Mass., 1972, pp 629-682.
2. For reviews, see (a) A. T. Nielsen and W. J. Houlihan, Org. Re
3. G. Wittig, Rec. Chem. Progr., 28, 45 (1967);
4. G. Wittig and A. Hesse, Org. Syn., 50, 66 (1970);
5. G. Wittig and H. Reiff, Angew. Chem., Int. Ed. Engl., 7, 7 (1968).
6. M. Stiles, J. Amer. Chem. Soc, 81, 2598 (1959);
7. M. Stiles and H. L. Finkbeiner, J. Amer. Chem. Soc, 81, 505 (1959);
8. R. L. Shriner, Org. React., 1, 1 (1942);
9. M. Mousseron, M. Mousseron-Canet, J. Neyrolles, and Y. Beziat, Bull. Soc. Chim. Fr., 1483 (1963);
10. J. Canceill, J. J. Basselier, and I. Jacques, Bull. Soc. Chim. Fr., 1024 (1967);
11. M. Bellassoued, R. Couffignal, and M. Gaudemar, C. R. Acad. Sci., Ser, C, 272, 1686 (1971), and earlier papers;
12. F. Lauria, V. Vecchietti, W. Logemann, G. Tosolini, and E. Dradi, Tetrahedron, 25, 3989 (1969);
13. W. R. Vaughan, S. C. Berstein, and M. E. Lorber, J. Org. Chem., 30, 1790 (1965);
14. W. R. Vaughan and H. P. Knoess, J. Org. Chem., 35, 2394 (1970).
15. T. A. Spencer, R. W. Britton, and D. S. Watt, J. Amer. Chem. Soc, 89, 5727 (1967).
16. For examples, see (a) A. T. Nielsen, C. Gibbons, and C. A. Zimmerman, J. Amer. Chem. Soc, 73, 4696 (1951);
17. H. E. Zimmerman and M. D. Traxler, J. Amer. Chem. Soc, 79, 1920 (1957);
18. T. Moriwake, J. Org. Chem., 31, 983 (1966);
19. J. A. Miller, M. H. Durand, and J. E. Dubois, Tetrahedron Lett., No. 32, 2831 (1965);
20. J. E. Dubois and J. Itzkowitch, Tetrahedron Lett., No. 32, 2839 (1965);
21. H. O. House, D. G. Melillo, and F. J. Sauter, J. Org. Chem., 38, 741 (1973).
22. C. R. Hauser and W. H. Puterbaugh, J. Amer. Chem. Soc, 75, 1068 (1953);
23. E. M. Kaiser and C. R. Hauser, J. Amer. Chem. Soc, 89, 4566 (1967);
24. M. W. Rathke, J. Amer. Chem. Soc, 92, 3222 (1970);
25. E. M. Kaiser, D. M. von Schriltz, and C. R. Hauser, J. Org. Chem., 32, 2610 (1967);
26. J. E. Dubois and M. Dubois, Bull. Soc. Chim. Fr., 3120, 3553 (1969);
27. J. E. Dubois and J. F. Fort, Tetrahedron, 28, 1653, 1665 (1972);
28. J. E. Dubois and P. Fellmann, C. R. Acad. Sci., Ser. C, 274, 1307 (1972).
29. For a recent summary with leading references, see H. O. House, M. Gall, and H. D. Olmstead, J. Org. Chem., 36, 2361 (1971).
30. For a study of the nmr spectrum of the bromomagnesium enolate (14b), see A. G. Pinkus, J. C. Lindberg, and A. B. Wu, Chem. Commun., 1350 (1969);
31. F. A. Cotton and G. Wilkinson, “Advanced Inorganic Chemistry,” 3rd ed, Interscience, New York, N. Y., 1972, p 52.
32. G. Stork and P. F. Hudrlik, J. Amer. Chem. Soc, 90, 4462, 4464 (1968).
33. H. Brockmann and H. Muxfeldt, Chem. Ber., 89, 1379 (1956).
34. M. Stiles, R. R. Winkler, Y. Chang, and L. Traynor, J. Amer. Chem. Soc, 86, 3337 (1964);
35. J. E. Dubois and M. Dobois, Bull. Soc. Chim. Fr., 3126 (1969);
36. J. J. Basselier, G. Gueremy, and S. Julia, Bull. Soc. Chim. Fr., 2988 (1965);
37. E. Kiehlmann and P. W. Loo, Can. J. Chem., 47, 2029 (1969).
38. H. O. House, L. J. Czuba, M. Gall, and H. D. Olmstead, J. Org. Chem., 34, 2324 (1969);
39. H. O. House, R. A. Auerbach, M. Gall, and N. P. Peet, J. Org. Chem., 38, 514 (1973);
40. H. O. House and M. J. Umen, J. Org. Chem., 38, 2841 (1973).
41. For a discussion of the applicability of conformational principles to metal chelates, see R. D. Gillard and H. M. Irving, Chem. Rev., 65, 603 (1965).
42. F. Iimura, Nippon Kagaku Zasshi, 77, 1846 (1956);
43. Chem. Abstr., 53, 2779 (1957);
44. A. I. Bol'shukhin and V. L. Zhitorcb, uk. J. Gen. Chem. USSR, 25, 1403 (1955).
45. F. G. Young, U. S. Patent 2, 461, 016 (1949);
46. Chem. Abstr., 43, 3838 (1949).
47. H. O. House and W. L. Respess, J. Organometal. Chem., 4, 95 (1965).
48. E. C. Ashby and R. C. Arnott, J. Organometal. Chem., 14, 1 (1968).
49. S. C. Watson and J. F. Eastham, J. Organometal. Chem., 9, 165 (1967).
50. K. N. Campbell, J. Amer. Chem. Soc, 59, 1980 (1937).
51. R. C. Fuson, W. O. Fugate, and C. H. Fisher, J. Amer. Chem. Soc., 61, 2362 (1939).
52. J. L. Guthrie and N. Rabjohn, J. Org. Chem., 22, 176 (1957).
53. E. P. Kohler, Amer. Chem. J., 38, 553 (1907).
54. R. C. Fuson and L. R. Melby, J. Amer. Chem. Soc., 75, 5402 (1953).
55. C. Schopf and K. Thierfelder, Justus Liebigs Ann. Chem., 518, 127 (1935).
56. St. von Kostanecki and G. Rossbach, Ber., 29, 1488 (1896).
57. K. Dimroth and W. Mach, Angew. Chem., Int. Ed. Engl, 7, 460 (1968).
58. P. D. Bartlett, M. Roha, and R. M. Stiles, J. Amer. Chem. Soc, 76, 2349 (1954);
59. J. Colonge, Bull. Soc. Chim. Fr., 57 (1935);
60. A. Bienveniie and J. E. Dubois, Bull. Soc. Chim. Fr., 391 (1969).
61. K. W. Bowers, R. W. Giese, J. Grimshaw, H. O. House, N. H. Kolodny, K. Kronberger, and D. K. Roe, J. Amer. Chem. Soc., 92, 2783 (1970).
62. E. Yoshisato and S. Tsutsumi, J. Amer. Chem. Soc, 90, 4488 (1968).
63. H. J. Shine and E. E. Turner, J. Inst. Petrol, London, 36, 73 (1950).
64. H. J. Backer and J. Strating, Reel. Trae. Chim. Pays-Bas, 56, 1069 (1937).
65. G. Kresze and B. Gnauck, Z. Electrochem., 60, 174 (1956);
66. H. E. Zimmerman and J. English, Jr., J. Amer. Chem. Soc, 76, 2285 (1954).
67. D. Vorlander and K. Kunze, Ber., 59, 2078, 2081 (1926).
68. An authentic sample of one stereoisomer of structure 43 is reported to melt at 210°: S. Julia and D. Veresch, Bull. Soc. Chim. Fr., 1127 (1959). This same material, mp 207-209°, has been studied subsequently:
69. M. N. Tilichenko and V. G. Kharchenko, Zh. Obshch. Khim., 29, 1909 (1959);
70. Chem. Abstr., 54, 9793 (1960);
71. J. Pitha, M. N. Tilichenko, and V. G. Kharchenko, Chem. Abstr., 34, 1936 (1964);
72. Chem. Abstr., 61, 8163 (1964).
73. N. S. Bhacca and D. H. Williams, “Applications of NMR Spectroscopy in Organic Chemistry,” Holden-Day, San Francisco, Calif., 1964, pp 159-182.
74. C. C. Hinckley, M. R. Klotz, and F. Patil, J. Amer. Chem. Soc, 93, 2417 (1971), and references therein;
75. R. E. Rondeau and R. E. Sievers, J. Amer. Chem. Soc, 93, 1522 (1971).