Stereo- and Regiocontrol by Complex Induced Proximity Effects: Reactions of Organolithium Compounds

Accounts of Chemical Research

Volumn 19, Issue 11, 1986, Pages 356-363

  Beak, Peter ^a   Meyers, A I ^b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2042487195     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar00131a005     Document Type: Article

References (46)

1. For recent discussions and diverse applications of this ubiquitous concept, see: (a) Menger, F. M. Acc. Chem. Res. 1985, 18, 128. (b) Weinreb, S. M. Acc. Chem. Res. 1985, 18, 16. Kozikowski, A. P. Acc. Chem. Res. 1984, 17, 410. Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P. Acc. Chem. Res. 1984, 17, 35. (c) Hibbert, F. Acc. Chem. Res. 1984, 17, 115. (d) Breslow, R. Acc. Chem. Res. 1980, 13, 170. (e) Mutterties, E. Chem. Soc. Rev. 1982, 11, 283. (f) Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y. D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Lancharich. Science 1986, 231, 1108. (g) Beak, P.; Ziegler, J. M. J. Org. Chem. 1981, 46, 614.
2. (a) Wakefield, B. J. Chemistry of Organolithium Compounds; Pergamon: Oxford, 1974. (b) Meyers, A. I. Acc. Chem. Res. 1978, 11, 375.
3. (a) Gschwend, H. W.; Rodriquez, H. R. Org. React. (N.Y.) 1979, 26, 1. H. Gilman [Gilman, H.; Marten, J. W. Org. React. N.Y. 1954, 8, 258] credits Roberts and Curtin [Roberts, J. D.; Curtin, D. Y. J. Am. Chem. Soc. 1946, 68, 1658, for demonstrating this effect in ortho lithiations. (b) Klumpp, G. W. Rec. Trav. Chim. Pays-Bas 1986, 105, 1.
4. For recent examples and leading references, see: Amstuz, R.; Laube, T; Schweizer, W. B.; Seebach, D.; Dunitz, J. D. Helv. Chim. Acta 1984, 67, 224. Jastrzebski, J. T. B. H.; van Koten, G.; Konijn, M.; Stem, C. H. J. Am. Chem. Soc. 1982, 104, 5490. Al-Aseer, M. A.; Allison, B. D.; Smith, S. G. J. Org. Chem. 1985, 50, 2715. Frankel, G.; Henrichs, M.; Hewitt, M.; Su, B. M. J. Am. Chem. Soc. 1984, 106, 255. Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373. Jackman, L. M.; Scormoutzous, L. M. J. Am. Chem. Soc. 1984, 106, 4627. Buese, M. A.; Hogen-Eisch, T. E. Helv. Chim. Acta. 1985, 107, 4509. McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Looli, H. R. Helv. Chim. Acta. 1985, 107, 1810. Kaufmann, E.; Clark, T.; Schleyer, P. v. R. J. Am. Chem. Soc. 1984, 106, 1856. Streitwieser, A., Jr. Acc. Chem. Res. 1984, 17, 353, and references cited therein.
5. a's of N,N-dimethylacetamide (34–35) and propene (44) from the work of Bordwell, Streitwieser, and Breslow.
6. Meyers, A. I.; Pansegrau, P. D. Tetrahedron Lett. 1983, 24, 4935; 1984, 25, 2941.
7. Hoffmann, R. W. Dehydrobenzenes and Cycloalkynes; Academic Press: New York, 1967.
8. Complex-induced proximity effects have been or can be invoked for a wide variety of reactions. Many reactions of allylic alcohols are considered to demonstrate such an effect. Examples include cyclo- by the Simmonds-Smith reagent [Staroscik, J. D.; Rickborn, B. J. Org. Chem. 1972, 37, 738], hydroboration [House, H. Modern Synthetic Reaction; W. A. Benjamin: New York, 1972; pp 115–117] and, hydrogenations catalyzed by iridium and rhodium [Evans D. A.; Morrissey, M. M. J. Am. Chem. Soc. 1984, 106, 3866]. Regio- and stereospecific reductions and alkylations of double bonds are also recent synthetically useful examples. Gammill, R. B.; Bell, L. T.; Nash, S. A. J. Org. Chem. 1984, 49, 3039. Moret, E.; Schlosser, M. Tetrahedron Lett. 1985, 4423. Iron and palladium insertion into sites remote from the directing functionality also illustrate CIPE process. For examples, see: Groves, J. T.; Subramanian, D. V. J. Amer. Chem. Soc. 1984, 106, 2177, Heumann, A.; Backvall, J. E. Angew. Chem. Int. Ed. Engl. 1985, 24, 207. Baldwin, J. E.; Jones, R. H.; Najera, C.; Yus, M. Tetrahedron 1985, 41, 699. Perhaps the most dramatic current example is the gas-phase insertion of cobalt into a carbon-carbon bond, postulated to involve initial complexation with an proximate hydroxyl group, Tsarbopoulos, A.; allison, J. J. Am. Chem. Soc. 1985, 107, 5085.
9. Patel, P.; Joule, J. A. J. Chem. Soc., Chem. Comm. 1985, 1021.
10. (a) Beak, P.; Bonham, J. J. Am. Chem. Soc. 1965, 87, 3365. (b) Beak, P.; Monroe, E. M. J. Org, Chem. 1964, 34, 589. (c) Meyers, A. I.; Kunnen, K., unpublished results.
11. Posner, G. H.; Lentz, C. M. J. Am. Chem. Soc. 1979, 101, 934.
12. For a more recent case and a suggestion of the importance of complexation, see: Majewski, M.; Green, T. R.; Snieckus, V. Tetrahedron Lett. 1986, 27, 531. For an example in which a sulfone group is suggested to be involved in a similar reaction, see: Block, E.; Eswarakrishnan, V.; Gebreges, K. Tetrahedron Lett. 1984, 25, 5469.
13. (a) Harris, F. L.; Weiler, L. Tetrahedron Lett. 1985, 26, 1939; 1984, 25, 1333. (b) Harris, F. L.; Weiler, L. J. Chem. Soc., Chem. Comm. 1985, 1124.
14. Beak, P.; Kempf, D. J.; Wilson, K. D. J. Am. Chem. Soc. 1985, 107, 4745.
15. Trost, B. M.; Vaultier, M.; Santiago, M. L. J. Am. Chem. Soc. 1980, 102, 7929.
16. Ekogha, C. B. B.; Ruel, O.; Julia, S. A. Tetrahedron Lett. 1983, 24, 4825, 4829.
17. (a) McDougal, P. G.; Rico, J. G. Tetrahedron Lett. 1984, 25, 5977. (b) Townsend, C. A.; Bloom, L. M. Tetrahedron Lett. 1981, 22, 3923. Winkle, M. R.; Ronald, R. C. J. Org. Chem. 1982, 47, 2101; For a recent example on cyclohexenyl metalation see: Stork, G.; Shiner, C.; Cheng, C. W.; Polt, R. L. J. Am. Chem. Soc. 1986, 108, 304.
18. MacDonald, T. L.; Narayanan, B. A. J. Org. Chem. 1983, 48, 1131.
19. Taylor, S. L.; Lee, D. Y.; Martin, J. C. J. Org. Chem. 1983, 43, 4158.
20. (a) Comins, D. L.; Brown, J. D.; Mantlo, N. B. Tetrahedron Lett. 1982, 23, 3979. (b) For a recent example of transient introduction of a complexing group in tetrahydroisoquinoline alkylations, see: Katritzky, A. R.; Akutagawa, K. Tetrahedron 1986, 42, 2571.
21. This technique was used earlier by Gschwend and co-workers for ortho metalation of N,N-dimethylbenzamides. Barsky, L.; Gschwend, H. W.; McKenna, J.; Rodriquez, H. R. J. Org. Chem. 1976, 41, 3651.
22. Lau, K. S. Y.; Schlosser, M. J. Org. Chem. 1978, 43, 1595.
23. Meyers, A. I.; Spohn, R. F. J. Org. Chem. 1985, 50, 4872.
24. Newman-Evans. R. H.; Carpenter, B. K. Tetrahedron Lett. 1985, 26, 1141.
25. Wittig, G.; Otlen, J. Tetrahedron Lett. 1963, 601.
26. Klumpp, G. W.; Veerkind, A. H.; deGraff, W. L.; Bickelhaupt, F. Justus Liebigs Ann. Chem. 1967, 706, 46.
27. Eisch, J. J.; Husk, G. R. J. Am. Chem. Soc. 1985, 89, 4194.
28. Cherest, M.; Felkin, H.; Frajerman, C.; Lion, C.; Roussi, G.; Swierczewski, G. Tetrahedron Lett. 1966, 875.
29. Eisch, J. J.; Merkley, J. H.; Galle, J. E. J. Org. Chem. 1979, 44, 587.
30. For a review, see: Vara Prasad, J. V. N.; Pillai, C. N. J. Organometall. Chem. 1983, 259, 1.
31. Crandall, J. K.; Clark, A. C. J. Org. Chem. 1972, 37, 4236. Richey, H. G., Jr; Heyn, A. S.; Erickson, W. F. J. Org. Chem. 1983, 48, 3821.
32. Felkin, H.; Swierczewski, G.; Tambute, A. Tetrahedron Lett. 1969, 707.
33. (a) Oppolozer, W.; Pitteloud, R.; Strauss, H. R. J. Am. Chem. Soc. 1982, 106, 6476. Oppolozer, W.; Heland, R. P. J. Am. Chem. Soc, 6478. (b) The reaction may occur with allyllithium reagents as well: Edwards, J. E.; McQuillin, W. H. J. Chem. Soc., Chem. Comm. 1977, 838.
34. (a) Klumpp, G. W.; Mierop, A. J. C.; Vrielink, J. J.; Brugman, A.; Schakel, M. J. Am. Chem. Soc. 1985, 107, 6740. For cases of normal Michael additions to secondary amides see: (b) Mpango, G. B.; Maha-lanabis, K. K.; Mahadavi-Damghani, Z.; Snieckus, V. Tetrahedron Lett. 1986, 21, 4823. (c) Kruthof, K. J. H.; Mateboer, A.; Schakel, M.; Klumpp, G. W. Recl. Trav. Chim. Pays-Bas 1986, 105, 63.
35. Kokko, B. J.; Beak, P. Tetrahedron Lett. 1983, 561, and references cited therein.
36. Beak, P.; Basha, A.; Kokko, B. J. Am. Chem. Soc. 1984, 106, 1511.
37. Boche, G. J. Chem. Soc., Chem. Comm. 1984, 1591. McKee, M. J. Am. Chem. Soc. 1985, 107, 859. Armstrong, D. R.; Smith, R.; Walker, G. T. J. Chem. Soc., Chem. Comm. 1985, 789.
38. Duraisamy, M.; Walborsky, H. M. J. Am. Chem. Soc. 1984, 106, 5035.
39. Boche, G.; Decker, G.; Etzrodt, H.; Mahdi, W.; Kos, A. J.; Schleyer, P. V. R. J. Chem. Soc., Chem. Comm. 1984, 1483. Posner, G. H.; Canella, K. A. J. Am. Chem. Soc. 1985, 107, 2571; Bates, R. B.; Gordan, B., III; Highsmith, J. H.; White, J. J. J. Org. Chem. 1984, 49, 298.
40. Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991.
41. Meyers, A. I.; Dickman, D. A.; Bailey, T. R. J. Am. Chem. Soc. 1985, 106, 7974.
42. Solid state and solution structures, which provide convincing evidence for complexation in ground states, can be extrapolated to effects in reactive species as strong but circumstantial support for mechanistic hypothesis. For a recent case, see: Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 98, 1373.
43. Wykypiel, W.; Lohmann, J.; Seebach, D. Helv. Chim. Acta 1981, 64, 1337; Beak, P.; Zajdel, W. J. J. Am. Chem. Soc. 1984, 106, 1010, and references cited therein.
44. (a) Al-Aseer, M.; Beak, P.; Hay, D.; Kempf, D. J.; Mills, S.; Smith, S. G. J. Am. Chem. Soc. 1983, 105, 2080. (b) Similar conclusions were drawn for α-lithio formamidines: Meyers, A. I.; Fuentes, L. M.; Rieker, W. F. J. Am. Chem. Soc. 1983, 105, 2082. (c) Fitt, J. J.; Gschwend, H. W. J. Org. Chem. 1984, 49, 209.
45. Rondan, N. G.; Houk, K. N.; Beak, P.; Zajdel, W. J.; Chandrasekhar, J.; Schleyer, P. V. R. J. Org. Chem. 1981, 46, 4316.
46. Miller, D. J.; Saunders, W. H., Jr. J. Org. Chem. 1982, 47, 5039.