Asymmetric [2,3]-sigmatropic rearrangement of allylic ammonium ylides

Journal of the American Chemical Society

Volumn 127, Issue 26, 2005, Pages 9352-9353

  Blid, Jan ^a   Panknin, Olaf ^a   Somfai, Peter ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMMONIUM DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 21644453480     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0510562     Document Type: Article

References (25)

1. Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamom: Oxford, 1991; Vol. 3, pp 913-974.
2. For recent examples, see: (a) Clark, J. S.; Hodgson, P. B.; Goldsmith, M. D.; Blake, A. J.; Cooke, P. A.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 2001, 3325-3337.
3. (b) Clark, J. S.; Middleton, M. D. Org. Lett. 2002, 4, 765-768.
4. (c) Roberts, E.; Sancon, J. P.; Sweeney, J. B.; Workman, J. A. Org. Lett. 2003, 5, 4775-4777.
5. (d) Zhou, C.-Y.; Yu, W.-Y.; Chan, P. W. H.; Che, C.-M. J. Org. Chem. 2004, 69, 7072-7082.
6. (a) Mageswaran, S.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1981, 1953-1962.
7. (b) Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1995, 339, 161-168.
8. (a) Kaiser, G. V.; Ashbrook, C. W.; Baldwin, J. E. J. Am. Chem. Soc. 1971, 93, 2342-2344.
9. (b) Hiroi, K.; Nakazawa, K. Chem. Lett. 1980, 1077-1080.
10. (c) Clark, J. S.; Hodgson, P. B. Tetrahedron Lett. 1995, 36, 2519-2522.
11. (d) Gawley, R. E.; Zhang, Q.; Campagna, S. J. Am. Chem. Soc. 1995, 117, 11817-11818.
12. (e) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31-33.
13. (f) Aggarwal, V. K.; Fans. G.; Charmant, J. P. H.; Meek, G. Org. Lett. 2003, 5, 1757-1760.
14. Workman, J. A.; Garrido, N. P.; Sançon, J.; Roberts, E.; Wessel, H. P.; Sweeney, J. B. J. Am. Chem. Soc. 2005, 127, 1066-1067.
15. Blid, J.; Brandt, P.; Somfai, P. J. Org. Chem. 2004, 69, 3043-3049.
16. Prior investigations of the Lewis acid-mediated [2,3]-sigmatropic rearrangement: (a) Murata, Y.; Nakai, K. Chem. Lett. 1990, 2069-2072.
17. (b) Kessar, S. V.; Singh, P.; Kaul, V. K.; Kumar, G. Tetrahedron Lett. 1995, 36, 8481-8484.
18. Coldham, I.; Middleton, M. L.; Taylor, P. L. J. Chem. Soc., Perkin Trans, 1 1998, 2817-2821.
19. Fujimoto, K.; Matsuhashi, C.; Nakai, T. Heterocycles 1996, 42, 423-435.
20. Care must be taken in order to exclude the formed HBr; see Supporting Information.
21. The ligand could be recovered almost quantitatively; see Supporting Information.
22. 2O, THF, or PhMe) did not improve the yield or enantiomeric excess.
23. The corresponding endo complexes are omitted for clarity.
24. Equilibration of diastereomeric oxazaborolidines has been described previously, see: Vedejs, E.; Fields. S. C.; Lin, S.; Sehrimpf, M. R. J. Org. Chem. 1995, 60, 3028-3034. Equilibration before deprotonation and rearrangement can also be envisioned.
25. 1 = H) at the B3LYP/6-31G* level of calculation. For computational details, see Supporting Information.