Oxovanadium(V)-catalyzed enantioselective Meerwein-Ponndorf-Verley cyanation of aldehydes using acetone cyanohydrin

Tetrahedron Letters

Volumn 45, Issue 33, 2004, Pages 6229-6233

  Watanabe, Akira ^a,b   Matsumoto, Kazuhiro ^c   Shimada, Yuya ^c   Katsuki, Tsutomu ^c  

^a KYUSHU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c NONE

Author keywords

Asymmetric catalysis; Cyanohydrin; Meerwein Ponndorf Verley cyanation; Oxovanadium(V)(salen) complex

Indexed keywords

ACETONE; ALDEHYDE; CYANOHYDRIN; OXOVANADIUM; UNCLASSIFIED DRUG; VANADIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CYANATION; MEERWEIN PONNDORF VERLEY REDUCTION; PROTON NUCLEAR MAGNETIC RESONANCE; SULFOXIDATION;

MOROCCAN PEPPER VIRUS;

EID: 3242772853     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.099     Document Type: Article

References (23)

1. (a) Mori, A.; Inoue, S. In Comprehensive Asymmetric Catalysis, Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp. 983-994
2. M. North Tetrahedron: Asymmetry 14 2003 147 176
3. J. Brunel and I. Holmes Angew. Chem. Int. Ed. 43 2004 2752 2778
4. M. Shibasaki and M. Kanai Chem. Pharm. Bull. 49 2001 511 524
5. M. Hayashi, Y. Miyamoto, T. Inoue and N. Oguni J. Org. Chem. 58 1993 1515 1522
6. X.-G. Zhou, J.-S. Huang, P.-H. Ko, K.-K. Cheng and C.-M. Che J. Chem. Soc., Dalton. Trans. 1999 3303 3309
7. T. Katsuki Synlett 2003 281 297
8. W. Pan, X. Feng, L. Gong, W. Hu, Z. Li, A. Mi and Y. Jiang Synlett 1996 337 338
9. Y. Belokon, N. Ikonnikov, M. Moscalenko, M. North, S. Orlova, V. Tararov and L. Yashkina Tetrahedron: Asymmetry 7 1996 851 855
10. S. Liang and X.R. Bu J. Org. Chem. 67 2002 2702 2704
11. Li(salen) has been used as a catalyst: I.P. Holmes and H.B. Kagan Tetrahedron Lett. 41 2000 7457 7460
12. Y. Belokon', S. Caveda-Cepas, B. Green, N. Ikonnikov, V. Khrustalev, V. Larichev, M. Moskalenko, M. North, C. Orizu, V. Tararov, M. Tasinazzo, G. Timofeeva and L. Yashkina J. Am. Chem. Soc. 121 1999 3968 3973
13. Y. Belokon', B. Green, N. Ikonnikov, V. Larichev, B. Lokshin, M. Moskalenko, M. North, C. Orizu, A. Peregudov and G. Timofeeva Eur. J. Org. Chem. 2000 2655 2661
14. Y. Belokon', B. Green, N. Ikonnikov, M. North, T. Parsons and V. Tararov Tetrahedron 57 2001 771 779
15. Y. Belokon', M. North and T. Parsons Org. Lett. 2 2000 1617 1619
16. T. Ooi, T. Miura, K. Takaya, H. Ichikawa and K. Maruoka Tetrahedron 57 2001 867 873
17. B. Saito and T. Katsuki Tetrahedron Lett. 42 2001 3873 3876
18. B. Saito and T. Katsuki Tetrahedron Lett. 42 2001 8333 8336
19. Zr(salen) complex catalyzes Baeyerâ€"Villiger reaction, in which a ketone and hydrogen peroxide are coordinated to the zirconium ion and reacted to give a chiral lactone: A. Watanabe, T. Uchida, K. Ito and T. Katsuki Tetrahedron Lett. 43 2002 4481 4485
20. A. Watanabe, T. Uchida, R. Irie and T. Katsuki Proc. Natl. Acad. Sci. USA 101 2004 5737 5742
21. K. Nakajima, K. Kojima, M. Kojima and J. Fujita Bull. Chem. Soc. Jpn. 63 1990 2620 2630
22. Y. Belokon’, P. Carta, A. Gutnov, V. Maleev, M. Moskalenko, L. Yashkina, N. Ikonnikov, N. Voskoboev, V. Khrustalev and M. North Helv. Chim. Acta 85 2002 3301 3312
23. 51V NMR study: V. Vergopoulos, S. Jantzen, D. Rodewald and D. Rehder J. Chem. Soc., Chem. Commun. 1995 377 378