Complex-Induced Proximity Effects: Stereoselective Carbon-Carbon Bond Formation in Chiral Auxiliary Mediated β-Lithiation-Substitution Sequences of β-Substituted Secondary Carboxamides

Journal of Organic Chemistry

Volumn 63, Issue 1, 1998, Pages 2-3

  Pippel, Daniel J ^a   Curtis, Michael D ^a   Du, Hua ^a   Beak, Peter ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001840864     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972042k     Document Type: Article

References (29)

1. (a) Beak, P.; Meyers, A. I. Acc. Chem. Res 1986, 19, 356.
2. (b) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res 1996, 29, 552.
3. Snieckus, V. Chem. Rev. (Washington, D.C.) 1990, 90, 879.
4. (a) Beak, P.; Du, H. J. Am. Chem. Soc. 1993, 115, 2516.
5. (b) Lutz, G. P.; Du, H.; Gallagher, D. J.; Beak, P. J. Org. Chem. 1996, 61, 4542.
6. (c) Gallagher, D. J.; Du, H.; Long, S. A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 11391.
7. (a) Fuhrer, W.; Gschwend, H. W. J. Org. Chem. 1979, 44, 1133.
8. (b) Houlihan, W. J.; Parrino, V. A.; Uike, Y. J. Org. Chem. 1981, 46, 4511.
9. (c) Yates, P.; Schwartz, D. A. Can. J. Chem. 1983, 61, 509.
10. (d) Clark, R. D.; Muchowski, J. M.; Fisher, L. E.; Flippin, L. A.; Repke, D. B.; Souchet, M. Synthesis 1991, 871.
11. (e) Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984.
12. (a) Frost, C.; Linnane, P.; Magnus, P.; Spyvee, M. Tetrahedron Lett. 1996, 37, 9139.
13. (b) Magnus, N.; Magnus, P. Tetrahedron Lett. 1997, 38, 3491.
14. (c) Linnane, P.; Magnus, N.; Magnus, P. Nature 1997, 385, 799.
15. The authors have deposited atomic coordinates for structures 7, 8, 15, and 17 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, U.K.
16. Chang, C.-J.; Fang, J.-M.; Liao, L.-F. J. Org. Chem. 1993, 58, 1754.
17. (a) Carstens, A.; Hoppe, D. Tetrahedron 1994, 50, 6097.
18. (b) Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 12218 and references therein.
19. The sense of optical rotation for (S)-16 in conjunction with the X-ray crystal structure of (3S,1′R)-15 corroborates a provisional literature assignment for (R)-16. Meyers, A. I.; Smith, R. K.; Whitten, C. E. J. Org. Chem. 1979, 44, 2250.
20. These results do not rule out an initial asymmetric deprotonation to give configuration ally labile lithiated intermediates.
21. (a) Basu, A.; Gallagher, D. J.; Beak, P. J. Org. Chem. 1996, 61, 5718.
22. (b) Hirsch, R.; Hoffmann, R. W. Chem. Ber. 1992, 125, 975.
23. (c) Hoffmann, R. W.; Julius, M.; Chemla, F.; Ruhland, T.; Frenzen, G. Tetrahedron 1994, 50, 6049.
24. This interpretation is provisional as it is possible that the diastereomeric intermediates are configurationally stable on the time scale of reaction with electrophile, but the activation energies for each diastereomer are not experimentally distinguished by this reaction.
25. (a) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657.
26. (b) Ahlbrecht, H.; Bonnet, G.; Enders, D.; Zimmermann, G. Tetrahedron Lett. 1980, 21, 3175.
27. (a) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496.
28. (b) Evans, D. A.; Dow, R. L.; Shih, T. L.; Takacs, J. M.; Zahler, R. J. Am. Chem. Soc. 1990, 112, 5290.
29. (c) Ager, D. J.; Prakash, L; Schaad, D. R. Chem. Rev. (Washington, D.C.) 1996, 96, 835 and references therein.