Modeling and Experiment Reveal an Unexpected Stereoelectronic Effect on Conformation and Scalar Couplings of α-Aminoorganostannanes, with Possible Relevance to the Tin-Lithium Exchange Reaction

Journal of Organic Chemistry

Volumn 68, Issue 22, 2003, Pages 8480-8484

  Santiago, Marcelina ^a,b   Low, Eddy ^a   Chambournier, Gilles ^a   Gawley, Robert E ^a,b  

^a University of Miami   (United States)

^b UNIVERSITY OF ARKANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIZATION; FREE RADICALS; SYNTHESIS (CHEMICAL);

CYCLOAROMATIZATION;

AROMATIC COMPOUNDS;

ALPHA AMINOORGANOSTANNANE DERIVATIVE; CARBON; LITHIUM; N METHYL 2 (TRIBUTYLSTANNYL)PIPERIDINE DERIVATIVE; NITROGEN; ORGANOTIN COMPOUND; PIPERIDINE DERIVATIVE; TIN; TRIBUTYLTIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL MODEL; CHEMISTRY; CONFORMATION; CONFORMATIONAL TRANSITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

CARBON ISOTOPES; LITHIUM; MODELS, CHEMICAL; MOLECULAR CONFORMATION; NITROGEN; NITROGEN ISOTOPES; ORGANOTIN COMPOUNDS; PIPERIDINES; TIN; TRIALKYLTIN COMPOUNDS;

EID: 0142258988     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034948y     Document Type: Article

References (38)

1. (a) Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon: 2002; Vol. 23.
2. (b) Hodgson, D. M., Ed. Organolithiums in Enantioselective Synthesis; Springer-Verlag: Heidelberg, 2003; Vol. 5.
3. (c) Rappoport, Z., Marek, I., Eds.; The Chemistry of Organolithium Compounds; Wiley: New York, 2003.
4. Gawley, R. E.; Coldham, I. In The Chemistry of Organolithium Compounds (Patai Series); Rappoport, Z., Marek, I., Eds.; Wiley: Chichester, 2003.
5. Gawley, R. E.; Zhang, Q. Tetrahedron 1994, 50, 6077-6088.
6. Coldham, I.; Dufour, S.; Haxell, T. F. N.; Howard, S.; Vennall, G. P. Angew. Chemie Int. Ed. Engl. 2002, 41, 3887-3889.
7. (a) Peterson, D. J.; Ward, J. F. J. Organomet. Chem. 1974, 66, 209-217.
8. (b) Peterson, D. J. J. Organomet. Chem. 1970, 21, P63-64.
9. (c) Peterson, D. J. J. Am. Chem. Soc. 1971, 93, 4027-4031.
10. Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620.
11. (a) Vedejs, E.; Moss, W. O. J. Am. Chem. Soc. 1993, 115, 1607-1608.
12. (b) Gawley, R. E.; Zhang, Q. J. Am. Chem. Soc. 1993, 115, 7515-7516.
13. (c) Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763-5769.
14. (d) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322-5323.
15. (a) Pearson, W. H.; Lindbeck, A. C. J. Am. Chem. Soc. 1991, 113, 8546-8548.
16. (b) Chong, J. M.; Park, S. B. J. Org. Chem. 1992, 57, 2220-2222.
17. (c) Pearson, W. H.; Lindbeck, A. C.; Kampf, J. W. J. Am. Chem. Soc. 1993, 1993, 2622-2636.
18. (d) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
19. (e) Colombo, L.; Di Giacomo, M.; Brusotti, G.; Delogu, G. Tetrahedron Lett. 1994, 35, 2063-2066.
20. (f) Colombo, L.; Di Giacomo, M.; Brusotti, G.; Milano, E. Tetrahedron Lett. 1995, 36, 2863-2866.
21. (g) Iula, D.; Gawley, R. E. J. Org. Chem. 2000, 65, 6196-6201.
22. Gawley, R. E.; Low, E.; Chambournier, G. Org. Lett. 1999, 1, 653-655.
23. Chambournier, G.; Gawley, R. E. Org. Lett. 2000, 1561-1564.
24. Low, E.; Gawley, R. E. J. Am. Chem. Soc. 2000, 122, 9562-9563.
25. Schneider, W.; Dillmann, R. Chem. Ber. 1963, 96, 2377-2386.
26. (a) Beak, P.; Lee, W.-K. Tetrahedron Lett. 1989, 30, 1197-1200.
27. (b) Beak, P.; Lee, W. K. J. Org. Chem. 1990, 55, 2578-2580.
28. Coldham, I.; Copley, R. C. B.; Haxell, T. F. N.; Howard, S. Org. Lett. 2001, 3, 3799-3801.
29. Eliel, E. L.; Wilen, S. H.; Mander, L. N. In Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 641-647.
30. Doddrell, D.; Burfitt, I.; Kitching, W.; Bullpitt, M.; Lee, C.-H.; Mynott, R. J.; Considine, J. L.; Kuivila, H. G.; Sarma, R. H. J. Am. Chem. Soc. 1974, 96, 1640-1642.
31. Kitching, W.; Olszowy, H.; Waugh, J.; Doddrell, D. J. Org. Chem. 1978, 43, 898-906.
32. Gil, V. M. S.; von Philipsborn, W. Magn. Reson. Chem. 1989, 27, 409-430.
33. Kitching, W.; Olszowy, H. A.; Harvey, K. J. Org. Chem. 1982, 47, 1893-1904.
34. Eliel, E. L.; Kandasamy, D.; Yen, C.; Hargrave, K. D. J. Am. Chem. Soc. 1980, 102, 3698-3707.
35. Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356-363.
36. Burchat, A. F.; Chong, J. M.; Park, S. B. Tetrahedron Lett. 1993, 34, 51-54.
37. Gawley, R. E.; Evanseck, J. D.; Pearson, W. H.; Stevens, E. P. In ECHET96. Electronic Conference on Heterocyclic Chemistry; Rzepa, H., Snyder, J., Eds.; Royal Society of Chemistry; www.ch.ic.ac.uk/ectoc/echet96.
38. Sawyer, J. S.; Kucerovy, A.; Macdonald, T. L.; McGarvey, G. J. J. Am. Chem. Soc. 1988, 110, 842-853.