Direct catalytic asymmetric addition of allylic cyanides to ketoimines

Journal of the American Chemical Society

Volumn 130, Issue 44, 2008, Pages 14477-14479

  Yazaki, Ryo ^a   Nitabaru, Tatsuya ^a   Kumagai, Naoya ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; IMINE; KETONE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHIRALITY; SYNTHESIS;

CATALYSIS; IMINES; KETONES; NITRILES; ORGANOPHOSPHORUS COMPOUNDS;

EID: 55549141880     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806572b     Document Type: Article

References (41)

1. For reviews, see: (a) Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363.
2. (b) Trost, B. M.; Jiang, C. Synthesis 2006, 369.
3. (c) Riant, O.; Hannedouche, J. Org. Biomol. Chem. 2007, 5, 873.
4. (a) Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Vallée, Y. Tetrahedron: Asymmetry 2001, 12, 1147.
5. (b) Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634.
6. (c) Wang, J.; Hu, X.; Jiang, J.; Gou, S.; Huang, X.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2007, 46, 8468, and references cited therein.
7. Wada, R.; Shibuguchi, T.; Makino, S.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7687.
8. (a) Saaby, S.; Nakama, K.; Lie, M. A.; Hazell, R. G.; Jørgensen, K. A. Chem. - Eur. J. 2003, 9, 6145.
9. (b) Suto, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 500.
10. (a) Lauzon, C.; Charette, A. B. Org. Lett. 2006, 8, 2743.
11. (b) Fu, P.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 5530.
12. Ting, A.; Schaus, S. E. Eur. J. Org. Chem. 2007, 5797, and references cited therein.
13. (a) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
14. (b) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
15. (c) Rueping, M.; Sugiono, E.; Moreth, S. A. Adv. Synth. Catal. 2007, 349, 759.
16. Zhuang, W.; Saaby, S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 4476.
17. (a) Ruano, J. L. G.; Topp, M.; López-Cantarero, J.; Alemán, J.; Remuiñán, M. J.; Cid, M. B. Org. Lett. 2005, 7, 4407.
18. (b) Pahadi, N. K.; Ube, H.; Terada, M. Tetarahedron Lett. 2007, 48, 8700.
19. For reviews: (a) Arseniyadis, S.; Kyler, K. S.; Watt, D. S. Org. React. 1984, 31, 1.
20. (b) Fleming, F. F.; Shook, B. C. Tetrahedron 2002, 58, 1.
21. (c) Fleming, F. F.; Iyer, P. S. Synthesis 2006, 893.
22. Selected examples on catalytic generation of active nucleophile from alkylnitriles: (a) Verkade, J. G.; Kisanga, P. B. Aldrichimica Acta 2004, 37, 3.
23. (b) Rodriguez, A. L.; Bunlaksananusorn, T.; Knochel, P. Org. Lett. 2000, 2, 3285.
24. (c) Suto, Y.; Tsuji, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 3757.
25. (d) Kumagai, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 13632.
26. (e) Fan, L.; Ozerov, O. V. Chem. Commun. 2005, 4450.
27. (f) Goto, A.; Endo, K.; Ukai, Y.; Irle, S.; Saito, S. Chem. Commun. 2008, 2212.
28. Calculated at the B3LYP/6-31G+(d,p) level. See Supporting Information for details.
29. (a) Kisanga, P. B.; Verkade, J. G. J. Org. Chem. 2002, 67, 426.
30. (b) Aydin, J.; Szabó, K. J. Org. Lett. 2008, 10, 2881.
31. (c) Swartz, B. D.; Reinartz, N. M.; Brennessel, W. W.; García, J. J.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 8548. See also ref 11a.
32. For a review, see: Weinreb, S. M.; Orr, R. K. Synthesis 2005, 1205.
33. An inexpensive C4 unit. $193.7/500 mL from TCI America as of Aug 2008.
34. Olefin geometry of major geometrical isomer was determined to be Z by NOE analysis. Isomerization of double bond was observed in aldol-type addition of allylic cyanide (refs 11a and 13a) and a direct Mannich-type reaction of β,γ-unsaturated ester; see: Yamaguchi, A.; Aoyama, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2007, 9, 3387.
35. Pilkington, C. J.; Zanotti-Gerosa, A. Org. Lett. 2003, 5, 1273.
36. 1H NMR and ESI-MS analysis. Analogous catalysts derived from Me or Et-BPE did not promote the reaction at all. For further discussions, see Supporting Information.
37. Formation of CuOAr upon addition of alkali metal aryloxide to Cu(I) salt; see: Eller, P. G.; Kubas, G. J. J. Am. Chem. Soc. 1977, 99, 4346.
38. For C- or N-bound nitrile nucleophile, see: Naota, T.; Tannna, A.; Kamuro, S.; Hieda, M.; Ogata, K.; Murahashi, S.-I.; Takaya, H. Chem.-Eur. J. 2008, 14, 2482, and references cited therein
39. For allylcopper nucleophile in asymmetric catalysis, see: Kanai, M.; Wada, R.; Shibuguchi, T.; Shibasaki, M. Pure Appl. Chem. 2008, 80, 1055, and references cited therein.
40. Formation of CuOAr upon addition of ArOH to arylcopper; see: Kubota, M.; Yamamoto, A. Bull Chem. Soc. Jpn. 1978, 51, 2909.
41. 4 was beneficial for the deprotonation process. Possibility (1) would be the most likely.