Is the A-ring of sparteine essential for high enantioselectivity in the asymmetric lithiation-substitution of N-Boc-pyrrolidine?

Journal of the American Chemical Society

Volumn 126, Issue 47, 2004, Pages 15473-15479

  Phuan, Puay Wah ^a   Ianni, James C ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ANALYSIS; STEREOCHEMISTRY;

LITHIATION-SUBSTITUTION; N-BOC-PYRROLIDINE; SPARTEINE;

LITHIUM;

DIAMINE; PYRROLIDINE DERIVATIVE; SPARTEINE;

ARTICLE; BIOTRANSFORMATION; CHIRALITY; ENANTIOSELECTIVITY; LITHIATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STEREOCHEMISTRY;

EID: 9644257027     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046321i     Document Type: Article

References (37)

1. For reviews, see: (a) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 56, 2282-2316. (b) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
2. For reviews, see: (a) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 56, 2282-2316. (b) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
3. (a) Harrison, J. R.; O'Brien, P.; Porter, D. W.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1999, 3623-3631.
4. (b) Harrison, J. R.; O'Brien, P.; Porter, D. W.; Smith, N. M. Chem. Commun. 2001, 1202-1203.
5. (c) Dearden, M. J.; Firkin, C. R.; Hermet, J.-P. R.; O'Brien, P. J. Am. Chem. Soc. 2002, 124, 11870-11871.
6. (d) Hermet, J.-P. R.; Porter, D. W.; Dearden, M. J.; Harrison, J. R.; Koplin, T.; O'Brien, P.; Parmene, J.; Tyurin, V.; Whitwood, A. C.; Gilday, J.; Smith, N. M. Org. Biomol. Chem. 2003, 1, 3977-3988.
7. (a) Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708-9710.
8. (b) Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872-5873.
9. (c) Beak, P.; Du, H. J. Am. Chem. Soc. 1993, 115, 2516-2518.
10. (d) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231-3239.
11. (e) Thayumanavan, S.; Lee, S.; Liu, C.; Beak, P. J. Am. Chem. Soc. 1994, 116, 9755-9756.
12. (f) Gallagher, D. J.; Beak, P. J. Org. Chem. 1995, 60, 7092-7093.
13. Danieli, B.; Lesma, G.; Passarella, D.; Piacenti, P.; Sacchetti, A.; Silvani, A.; Virdis, A. Tetrahedron Lett. 2002, 43, 7155-7158.
14. Spieler, J.; Huttenloch, O.; Waldmann, H. Eur. J. Org. Chem. 2000, 391-399.
15. Harrison, J. R.; O'Brien, P. Tetrahedron Lett. 2000, 41, 6161-6165.
16. Krasnov, V. P.; Levit, G. L.; Andreeva, I. N.; Grishakov, A. N.; Charushin, V. N.; Chupakhin, O. N. Mendeleev Commun. 2002, 12, 27-28.
17. For an overview, see: Hansch, C.; Leo, A. Exploring QSAR. Volume I.: Fundamentals, and Applications in Chemistry and Biology; American Chemical Society: Washington, DC, 1995.
18. For the first application of non-CoMFA QSAR type analyses to an asymmetric reaction, see: Oslob, J. D.; Akermark, B.; Helquist, P.; Norrby, P.-O. Organometallics 1997, 16, 3015-3021.
19. For an overview, see: Kubinyi, H. In Encyclopedia of Computational Chemistry: Schleyer, P. v. R., Ed.; Wiley: New York, 1998; Vol. 1, pp 448-460.
20. Kozlowski, M. C.; Dixon, S. L.; Panda, M.; Lauri, G. J. Am. Chem. Soc. 2003, 125, 6614-6615.
21. Subsequently, two other groups described CoMFA QSAR techniques with respect to chiral catalysts. However, these reports relied on molecular mechanics methods, not necessarily appropriate for organometallic catalysts, and did not describe predictions made prior to an experimental determination, (a) Lipkowitz, K. B.; Pradhan, M. J. Org. Chem. 2003, 68, 4648-4656. (b) Alvarez, S.; Schefzick, S.; Lipkowitz, K.; Avnir, D. Chem. Eur. J. 2003, 9, 5832-5837. (c) Hoogenraad, M.; Klaus, G. M.; Elders, N.; Hooijschuur, S. M.; McKay, B.; Smith, A. A.; Damen, E. W. P. Tetrahedron: Asymmetry 2004, 15, 519-523.
22. Subsequently, two other groups described CoMFA QSAR techniques with respect to chiral catalysts. However, these reports relied on molecular mechanics methods, not necessarily appropriate for organometallic catalysts, and did not describe predictions made prior to an experimental determination, (a) Lipkowitz, K. B.; Pradhan, M. J. Org. Chem. 2003, 68, 4648-4656. (b) Alvarez, S.; Schefzick, S.; Lipkowitz, K.; Avnir, D. Chem. Eur. J. 2003, 9, 5832-5837. (c) Hoogenraad, M.; Klaus, G. M.; Elders, N.; Hooijschuur, S. M.; McKay, B.; Smith, A. A.; Damen, E. W. P. Tetrahedron: Asymmetry 2004, 15, 519-523.
23. Subsequently, two other groups described CoMFA QSAR techniques with respect to chiral catalysts. However, these reports relied on molecular mechanics methods, not necessarily appropriate for organometallic catalysts, and did not describe predictions made prior to an experimental determination, (a) Lipkowitz, K. B.; Pradhan, M. J. Org. Chem. 2003, 68, 4648-4656. (b) Alvarez, S.; Schefzick, S.; Lipkowitz, K.; Avnir, D. Chem. Eur. J. 2003, 9, 5832-5837. (c) Hoogenraad, M.; Klaus, G. M.; Elders, N.; Hooijschuur, S. M.; McKay, B.; Smith, A. A.; Damen, E. W. P. Tetrahedron: Asymmetry 2004, 15, 519-523.
24. Gallagher, D. J.; Wu, S.; Nikolic, N. A.; Beak, P. J. Org. Chem. 1995, 60, 8148-8154.
25. Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875-878.
26. Kozlowski, M. C.; Xu, Z.; Santos, A. G. Tetrahedron 2001, 57, 4537-4542.
27. Dixon, S. L.; Merz, K. M., Jr.; Lauri, G.; Ianni, J. J. Comput. Chem. Accepted.
28. Dixon, S. L.; Merz, K. M., Jr. J. Chem. Phys. 1997, 107, 879-893.
29. Ianni, J.; Kozlowski, M. C. Manuscript in preparation. See the Supporting Information for a description of the G-QSAR program and its implementation.
30. For a discussion of the errors in transition structure calculations as they relate to stereoselectivity predictions, see: Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479.
31. See also the following article in this issue (ja046834p): O'Brien, P.; Wiberg, K. B.; Bailey, W. F.; Hermet, J.-P. R.; McGrath, M. J. J. Am. Chem. Soc. 2004, 124, 15480-15489 (JA046834p).
32. (a) Wiberg, K. B.; Bailey, W. F. Angew. Chem., Int. Ed. 2000, 39, 2127-2129.
33. (b) Wiberg, K. B.; Bailey, W. F. J. Am. Chem. Soc. 2001, 123, 8231-8238.
34. For related calculations in the asymmetric deprotonation of achiral alkyl carbamates, see: Würthwein, E.-U.; Behrens, K.; Hoppe, D. Chem. Eur. J. 1999, 5, 3459-3463.
35. Gross, K. M. B.; Beak, P. J. Am. Chem. Soc. 2001, 123, 315-321.
36. (a) Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49-56.
37. (b) Peng, C.; Schlegel, H. B. Isr. J. Chem. 1994, 33, 449-454.