An enantioselective organocatalytic oxidative dearomatization strategy

Journal of the American Chemical Society

Volumn 130, Issue 2, 2008, Pages 404-405

  Vo, Ngoc T ^a   Pace, Robert D M ^a   O'Hara, Fionn ^a   Gaunt, Matthew J ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIZATION; ARTICLE; CATALYSIS; DIASTEREOISOMER; ENANTIOSELECTIVITY; OXIDATION; SYNTHESIS; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

AROMATIC HYDROCARBON; PHENOL DERIVATIVE;

CATALYSIS; HYDROCARBONS, AROMATIC; OXIDATION-REDUCTION; PHENOLS; STEREOISOMERISM;

EID: 40149104139     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077457u     Document Type: Article

References (28)

1. For reviews of dearomatization methods, see: (a) Bach, T. Angew. Chem., Int. Ed. 1996, 35, 729.
2. (b) Rabideau, P. W.; Marcinow, Z. Org. React. 1992, 42, 1.
3. (c) Cornelisse, J. Chem. Rev. 1993, 93, 615.
4. Paradisi, C. In Comprehensive Organic Synthesis; Semmelhack, M. F., Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p 423.
5. For a recent examples of reductive dearomatization methods, see: (a) Clayden, J.; Dufour, J.; Grainger, D. M.; Helliwell, M. J. Am. Chem. Soc. 2007, 129, 7488.
6. (b) Clayden, J.; Stravinsky: Total synthesis of kanoids by dearomatizing anionic cyclization. In Strategies and Tactic in Organic Synthesis; Harmata, M., Ed.; Academic Press: 2004; Vol. 4, p 72.
7. Pelter, A., Elgendy, S. M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1891.
8. For selected examples of oxidative dearomatization in synthesis, see: (a) Gagnepain, J.; Castet, F.; Quideau, S. Angew. Chem., Int. Ed. 2007, 46, 1533.
9. (b) Cook, S. P.; Polara, A.; Danishefsky, S. J. J. Am. Chem. Soc. 2006, 128, 16440.
10. (c) Mejorado, L. H.; Pettus, T. R. R. J. Am. Chem. Soc. 2006, 128, 15625.
11. (d) Scheffler, G.; Seike, H.; Sorensen, E. J. Angew. Chem., Int. Ed. 2000, 39, 4593.
12. (e) Berube, A.; Drutu, I.; Wood, J. L. Org. Lett. 2006, 8, 5421.
13. (f) Zhu, J.; Porco, J. A., Jr. Org. Lett. 2006, 8, 5169.
14. (a) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184.
15. (b) Hayashi, Y.; Gotoh, H.; Tamura, T.; Yamaguchi, H.; Masui, R.; Shoji, M. J. Am. Chem. Soc. 2005, 127, 16028.
16. (c) Liu, Q.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 2552.
17. For an overview of catalytic cascade approaches to complex molecules synthesis, see: Walji, A. M.; MacMillan, D. W. C. Synlett, 2007, 1477.
18. For selected organocatalytic examples, see: (a) Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051.
19. (b) Enders, D. Hüttl, M. R. M.; Grondal, C.; Raabe, G. Nature, 2006, 441, 861.
20. (c) Carlone, A.; Cabrera, S.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1101.
21. (d) Zhou, J.; List, B. J. Am. Chem. Soc. 2007, 129, 7498.
22. For a recent review, see: Gaunt, M. J.; Johanssen, C. C. C.; McNally, A.; Vo, N. T. Drug. Disc. Today 2007, 12, 8 and references therein.
23. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
24. For an overview of the use of catalyst 3b, see: Palomo, C.; Mielgo, A. Angew. Chem., Int. Ed. 2006, 45, 7876 and references therein.
25. The oxidation is the "yield limiting" factor and the cyclization proceeds almost quantitatively in the stepwise case. See Supporting Information for further details.
26. (a) The dr is 3:1 after reaction, but equilibration at room temp gives 1:15 (-)-4d. (b) Absolute stereochemistry was confirmed by X-ray diffraction.
27. Canesi, S.; Bouchu, D.; Ciufolini, M. A. Org. Lett. 2005, 7, 175.
28. (b) Karam, O.; Anges, M, -M.; Jouannetaud, M.-P.; Jacquesy, J.-C.; Cousson, A. Tetratedron, 2004, 60, 6629.