Catalytic Asymmetric 1,4-Addition Reactions of Simple Alkylnitriles

Chemistry - An Asian Journal

Volumn 10, Issue 10, 2015, Pages 2143-2146

  Yamashita, Yasuhiro ^a   Sato, Io ^a   Suzuki, Hirotsugu ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

1,4 addition; asymmetric synthesis; catalyst; nitrile; strong base

Indexed keywords

CARBON; CATALYSTS; CHEMICAL ACTIVATION;

1 ,4-ADDITION; 1 ,4-ADDITION REACTIONS; ASYMMETRIC CARBONS; ASYMMETRIC SYNTHESIS; DIASTEREO- AND ENANTIOSELECTIVITY; NITRILE; STRONG BASE; UNSATURATED AMIDES;

CROWN ETHERS;

NITRILE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND;

CATALYSIS; HYDROGEN BONDING; MOLECULAR STRUCTURE; NITRILES;

EID: 84942364706     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201500405     Document Type: Article

References (40)

1. Comprehensive Organic Synthesis (Ed.:, B.M. Trost,), Pergamon Press, Oxford, 1991;
2. Comprehensive Organic Synthesis, 2nded., (Eds.:, P. Knochel, G.A. Molander,), Elsevier Science, 2014.
3. Handbook of Green Chemistry (Ed.:, P.T. Anastas,), Wiley-VCH, Weinheim, 2009;
4. S. Kobayashi, R. Matsubara, Chem. Eur. J. 2009, 15, 10694-10700.
5. For a recent review on catalytic asymmetric direct-type reactions under proton transfer conditions, see:, N. Kumagai, M. Shibasaki, Angew. Chem. Int. Ed. 2011, 50, 4760-4772;
6. Angew. Chem. 2011, 123, 4856-4868.
7. R. C. Larock, Comprehensive Organic Transformations, 2nded., Wiley-VCH, 1999.
8. F. G. Bordwell, Acc. Chem. Res. 1988, 21, 456. Also see:
9. Bordwell pKa table (http://www.chem.wisc.edu/areas/reich/pkatable/index.htm).
10. S. Arseniyadis, K. S. Kyler, D. S. Watt, Org. React. 1984, 31, 1;
11. F. F. Fleming, B. C. Shook, Tetrahedron 2002, 58, 1-23;
12. J. G. Verkade, P. B. Kisanga, Aldrichimica Acta 2004, 37, 3-14.
13. B. A. D′Sa, P. Kisanga, J. G. Verkade, J. Org. Chem. 1998, 63, 3961-3967;
14. P. Kisanga, D. McLeod, B. D′Sa, J. G. Verkade, J. Org. Chem. 1999, 64, 3090-3094;
15. P. Kisanga, J. G. Verkade, J. Org. Chem. 2000, 65, 5431-5432;
16. P. Kisanga, J. G. Verkade, Tetrahedron 2001, 57, 467-475;
17. J. G. Verkade, P. Kisanga, Tetrahedron 2003, 59, 7819-7858.
18. A. L. Rodriguez, T. Bunlaksananusorn, P. Knochel, Org. Lett. 2000, 2, 3285-3287.
19. Y. Suto, N. Kumagai, S. Matsunaga, M. Shibasaki, Org. Lett. 2003, 5, 3147-3150;
20. N. Kumagai, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 13632-13633;
21. Y. Suto, R. Tsuji, M. Kanai, M. Shibasaki, Org. Lett. 2005, 7, 3757-3760;
22. N. Kumagai, S. Matsunaga, M. Shibasaki, Chem. Commun. 2005, 3600-3602;
23. N. Kumagai, S. Matsunaga, M. Shibasaki, Tetrahedron 2007, 63, 8598-8608;
24. Y. Kawato, N. Kumagai, M. Shibasaki, Chem. Commun. 2013, 49, 11227-11229;
25. D. Sureshkumar, V. Ganesh, N. Kumagai, M. Shibasaki, Chem. Eur. J. 2014, 20, 15723-15726.
26. L. Fan, O. V. Ozerov, Chem. Commun. 2005, 4450-4452.
27. A. Goto, K. Endo, Y. Ukai, S. Irle, S. Saito, Chem. Commun. 2008, 2212-2214;
28. A. Goto, H. Naka, R. Noyori, S. Saito, Chem. Asian J. 2011, 6, 1740-1743.
29. S. Chakraborty, Y. J. Patel, J. A. Krause, H. Guan, Angew. Chem. Int. Ed. 2013, 52, 7523-7526;
30. Angew. Chem. 2013, 125, 7671-7674.
31. T. Poisson, V. Gembus, S. Oudeyer, F. Marsais, V. Levacher, J. Org. Chem. 2009, 74, 3516-3519.
32. T. Deng, H. Wang, C. Cai, Eur. J. Org. Chem. 2014, 7259-7264.
33. Y. Yamashita, H. Suzuki, S. Kobayashi, Org. Biomol. Chem. 2012, 10, 5750-5752;
34. H. Suzuki, I. Sato, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 2015, 137, 4336-4339.
35. See also ref.13 as a related example.
36. C. H. Heathcock, D. A. Oare, J. Org. Chem. 1985, 50, 3022-3024;
37. C. H. Heathcock, M. H. Norman, D. E. Uehling, J. Am. Chem. Soc. 1985, 107, 2797-2799.
38. D. Enders, A. Plant, Synlett 1994, 1054-1056;
39. M. Amat, M. Pérez, N. Llor, J. Bosch, E. Lago, E. Molins, Org. Lett. 2001, 3, 611-614;
40. J.-P. Chen, C.-H. Ding, W. Liu, X.-L. Hou, L.-X. Dai, J. Am. Chem. Soc. 2010, 132, 15493-15495.