Synthesis and Reactivity of Conformationally Locked α-Aminoorganostannanes and α-Aminoorganolithiums. Discovery of a Surprising Configurational Requirement for Transmetalation

Organic Letters

Volumn 2, Issue 11, 2000, Pages 1561-1564

  Chambournier, Gilles ^a   Gawley, Robert E ^a  

^a University of Miami   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM; ORGANOMETALLIC COMPOUND; ORGANOTIN COMPOUND; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; METABOLISM;

LITHIUM; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; ORGANOTIN COMPOUNDS; PIPERIDINES;

EID: 0034203317     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005770u     Document Type: Article

References (22)

1. Reviews: (a) Beak, P.; Reitz, B. D. Chem. Rev. 1978, 78, 275. (b) Beak, P.; Zajdel, W. J.; Reitz, B. D. Chem. Rev. 1984, 84, 471. (c) Gawley, R. E.; Rein, K. S. In Comprehensive Organic Synthesis; Trost B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991: Vol. 3, Chapter 1.2. (d) Gawley, R. E. Curr. Org. Chem. 1997, 1, 71.
2. Reviews: (a) Beak, P.; Reitz, B. D. Chem. Rev. 1978, 78, 275. (b) Beak, P.; Zajdel, W. J.; Reitz, B. D. Chem. Rev. 1984, 84, 471. (c) Gawley, R. E.; Rein, K. S. In Comprehensive Organic Synthesis; Trost B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991: Vol. 3, Chapter 1.2. (d) Gawley, R. E. Curr. Org. Chem. 1997, 1, 71.
3. Reviews: (a) Beak, P.; Reitz, B. D. Chem. Rev. 1978, 78, 275. (b) Beak, P.; Zajdel, W. J.; Reitz, B. D. Chem. Rev. 1984, 84, 471. (c) Gawley, R. E.; Rein, K. S. In Comprehensive Organic Synthesis; Trost B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991: Vol. 3, Chapter 1.2. (d) Gawley, R. E. Curr. Org. Chem. 1997, 1, 71.
4. Reviews: (a) Beak, P.; Reitz, B. D. Chem. Rev. 1978, 78, 275. (b) Beak, P.; Zajdel, W. J.; Reitz, B. D. Chem. Rev. 1984, 84, 471. (c) Gawley, R. E.; Rein, K. S. In Comprehensive Organic Synthesis; Trost B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991: Vol. 3, Chapter 1.2. (d) Gawley, R. E. Curr. Org. Chem. 1997, 1, 71.
5. (a) Gawley, R. E.; Zhang, Q. J. Am. Chem. Soc. 1993, 115, 7515.
6. (b) Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763.
7. (c) Gawley, R. E.; Zhang, Q. Z. Tetrahedron 1994, 50, 6077.
8. Gawley, R. E. Tetrahedron Lett. 1999, 40, 4297.
9. Gössinger, E. Monatsh. Chem. 1982, 113, 339.
10. (a) Beak, P.; Lee, W.-K. J. Org. Chem. 1990, 55, 2578.
11. (b) Beak, P.; Lee, W.-K. J. Org. Chem. 1993, 58, 1109.
12. Gawley, R. E.; Low, E.; Chambournier, G. Org. Lett. 1999, 1, 653.
13. (a) Meyers, A. I.; Shawe, T. T.; Gottlieb, L. Tetrahedron Lett. 1992, 33, 867.
14. (b) Gottlieb, L.; Meyers, A. I. Tetrahedron Lett. 1990, 33, 4723.
15. (c) Wilkinson, T. J.; Stehle, N. W.; Beak, P. Org. Lett. 2000, 2, 155.
16. Gawley, R. E.; Low, E.; Zhang, Q.; Harris, R. J. Am. Chem. Soc. 2000, 122, 3344.
17. (a) Tsunoda, T.; Fujiwara, K.; Yamamoto, Y.; Itô, S. Tetrahedron Lett. 1991, 32, 1975.
18. (b) Burchat, A. F.; Chong, J. M.; Park, S. B. Tetrahedron Lett. 1993, 34, 51.
19. (c) 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 Society of Chemistry: London, 1997 (CD-ROM).
20. (a) Kitching, W.; Olszowy, H.; Waugh, J.; Doddrell, D. J. Org. Chem. 1978, 43, 898.
21. (b) Kitching, W.; Olszowy, H. A.; Harvey, K. J. Org. Chem. 1982, 47, 1893.
22. 3Sn group in a flagpole orientation. Since this orientation would be of extraordinarily high energy, the 123°/126° torsions are more likely. This angle is close to an eclipsing angle of 120°, suggesting a flattened ring (half-chair). For 19, the solutions to the Kitching/Karplus equation correspond to possible torsions of 64° or 107°. Previously, we interpreted these data in terms of a relatively undistorted chair with an axial tin, but the 107° value cannot be completely ruled out. (Matrix Presented)