Guanidine-catalyzed asymmetric trimethylsilylcyanation of carbonyl compounds

Advanced Synthesis and Catalysis

Volumn 347, Issue 11-13, 2005, Pages 1653-1658

  Kitani, Yukari ^a   Kumamoto, Takuya ^a   Isobe, Toshio ^b   Fukuda, Keiko ^b   Ishikawa, Tsutomu ^a  

^a CHIBA UNIVERSITY   (Japan)

^b Shiratori Pharmaceutical Co Ltd   (Japan)

Author keywords

Asymmetric catalysis; Cyanotrimethylsilane; Guanidines; Hydrocyanation; Nitriles; Organic catalysis

Indexed keywords

EID: 27544472739     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505161     Document Type: Article

References (37)

1. a) M. B. Smith, J. March, March's Advanced Organic Chemistry, 5th edn., John Wiley & Sons, Inc. New York, 2001, pp 1239-1240;
2. b) M. North, in: Science of Synthesis, (Ed.: S.-I. Murahashi), Thieme, Stuttgart, 2004, Vol. 19, pp. 235-284.
3. W. C. Groutas, D. Felker, Synthesis 1980, 861-868;
4. J. K. Rasmussen, S. M. Heilmann, L. Krepski, Adv. Silicon Chem. 1991, 1, 65-187;
5. S. S. Kim, G. Rajagopal, D. H. Song, J. Org. Met. Chem. 2004, 689, 1734-1738.
6. a) T. Mukaiyama, S. Hayakawa, T. Yamada, N. Iwasawa, K. Narasaka, Bull. Chem. Soc. Jpn 1988, 61, 4379-4383;
7. b) S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 537-540, 541-544;
8. c) M. Hayashi, Y. Miyamoto, T. Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522;
9. d) E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004;
10. e) C. Bolm, P. Muller, Tetrahedron Lett. 1995, 36, 1625-1628;
11. f) Y. Belokon, M. Flego, N. Ikonnikov, M. Moscalenko, M. North, C. Orizu, V. Tararov, M. Tasinazzo, J. Chem. Soc. Perkin, Trans. 1 1997, 1293-1296;
12. g) M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, K. Smith, Tetrahedron: Asymmetry 1997, 8, 3939-3946;
13. h) V. I. Tararov, D. E. Hibbs, M. B. Hursthouse, N. S. Ikonnikov, K. M. A. Abdul Malik, M. North, C. Orizu, Y. N. Belokon, Chem. Commun. 1998, 387-388;
14. i) Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641-2642;
15. j) Y. N. Belokon, B. Green, N. S. Ikonnikov, M. North, T. Parson, V. I. Tararov, Tetrahedron 2001, 57, 771-779;
16. k) Y. Hamashima, D. Sawada, H. Nogami, M. Kanai, M. Shibasaki, Tetrahedron 2001, 57, 805-814;
17. l) H. Deng, M. P. Isler, M. L. Snapper, A. H. Hoveyda, Angew. Chem. Int. Ed. 2002, 41, 1009-1012;
18. m) F. Chen, X. Feng, B. Qin, G. Zhang, Y. Jiang, Org. Lett. 2003, 5, 949-952;
19. n) G. J. Rowlands, Synlett 2003, 236-240.
20. G. A. Olah, A. Burrichter, G. Rasul, M. Machoumy, G. K. S. Prakash, J. Am. Chem. Soc. 1997, 119, 12929-12933;
21. M. Costa, G. P. Chiusoli, D. Taffurelli, G. Dalmonego, J. Chem. Soc. Perkin Trans. 1 1998, 1541-1546;
22. B. Kovacevic, A. B. Maksic, Org. Lett. 2001, 3, 1523-1526.
23. Y. Yamamoto, S. Kojima, in: The Chemistry of Amidines and Imidines, (Eds.: S. Patai. Z. Rappoport), John Wiley & Sons Inc. New York, 1991, Vol. 2, pp 485-526.
24. a) T. Isobe, K. Fukuda, T. Ishikawa, J. Org. Chem. 2000, 65, 7770-7773;
25. b) T. Isobe, K. Fukuda, T. Tokunaga, H. Seki, K. Yamaguchi, T. Ishikawa, J. Org. Chem. 2000, 65, 7774-7778;
26. c) T. Isobe, K. Fukuda, K. Yamaguchi, H. Seki, T. Tokunaga, T. Ishikawa, J. Org. Chem. 2000, 65, 7779-7785.
27. T. Isobe, K. Fukuda, T. Ishikawa, Tetrahedron: Asymmetry 1998, 9, 1729-1735;
28. T. Isobe, K. Fukuda, Y. Araki, T. Ishikawa, Chem. Commun. 2001, 243-244;
29. T. Ishikawa, Y. Araki, K. Kumamoto, H. Seki, K. Fukuda, T. Isobe, Chem. Commun. 2001, 245-246;
30. T. Ishikawa, T. Isobe, Chem. Eur. J. 2002, 8, 552-557;
31. T. Ishikawa, T. Isobe, J. Synth. Org. Chem. Jpn 2003, 61, 58-66.
32. E. J. Corey, M. J. Grogan, Org. Lett. 1999, 1, 157-160.
33. a) T. Isobe, T. Ishikawa, J. Org. Chem. 1999, 64, 5832-5835;
34. T. Isobe, T. Ishikawa, J. Org. Chem. 1999, 64, 6984-6988;
35. T. Isobe, T. Ishikawa, J. Org. Chem. 1999, 64, 6989-6992.
36. For example, P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, Oxford, 1998.
37. The presence of rotational isomers should cause a broadening of signals under the measurement conditions.