Catalytic, Asymmetric Synthesis of Cyanohydrin Ethyl Carbonates

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4505-4507

  Belokon, Yuri N ^a   Blacker, A John ^b   Clutterbuck, Lisa A ^c   North, Michael ^c  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b Avecia Biologics Limited   (United Kingdom)

^c KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONIC ACID DERIVATIVE; CYANOHYDRIN; SALICYLALDEHYDE; TITANIUM DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; ENANTIOMER; SYNTHESIS;

EID: 0344496716     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035828f     Document Type: Article

References (18)

1. For a comprehensive review, see: North, M. Tetrahedron: Asymmetry 2003, 14, 147-176.
2. (a) Belokon', Y. N.; Caveda-Cepas, S.; Green, B.; Ikonnikov, N. S.; Khrustalev, V. N.; Larichev, V. S.; Moscalenko, M. A.; North, M.; Orizu, C.; Tararov, V. I.; Tasinazzo, M.; Timofeeva, G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999, 121, 3968-73.
3. (b) Belokon', Y. N.; Green, B.; Ikonnikov, N. S.; Larichev, V. S.; Lokshin, B. V.; Moscalenko, M. A.; North, M.; Orizu, C.; Peregudov, A. S.; Timofeeva, G. I. Eur. J. Org. Chem. 2000, 2655-61.
4. (a) Belokon', Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Tararov, V. I. Tetrahedron Lett. 1999, 40, 8147-50.
5. (b) Belokon', Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Parsons, T. ; Tararov, V. I. Tetrahedron 2001, 57, 771-9.
6. (a) Belokon, Y. N.; Gutnov, A. V.; Moskalenko, M. A.; Yashkina, L. V.; Lesovoy, D. E.; Ikonnikov, N. S.; Larichev, V. S.; North, M. Chem. Commun. 2002, 244-5.
7. (b) Belokon, Y. N.; Carta, P.; Gutnov, A. V.; Maleev, V.; Moskalenko, M. A.; Yashkina, L. V.; Ikonnikov, N. S.; Voskoboev, N. V.; Khrustalev, V. N.; North, M. Helv. Chim. Acta 2002, 85, 3301-12.
8. See for examples: (a) Okimoto, M.; Chiba, T. Synthesis 1996, 1188-1190. (b) Poirier, D.; Berthiaume, D.; Boivin, R. P. Synlett 1999, 1423-1425. (c) Berthiaume, D.; Poirier, D. Tetrahedron 2000, 56, 5995-6003. (d) Deardorff, D. R.; Taniguchi, C. M.; Tafti, S. A.; Kim, H. Y.; Choi, S. Y.; Downey, K. J.; Nguyen, T. V. J. Org. Chem. 2001, 66, 7191-7194.
9. See for examples: (a) Okimoto, M.; Chiba, T. Synthesis 1996, 1188-1190. (b) Poirier, D.; Berthiaume, D.; Boivin, R. P. Synlett 1999, 1423-1425. (c) Berthiaume, D.; Poirier, D. Tetrahedron 2000, 56, 5995-6003. (d) Deardorff, D. R.; Taniguchi, C. M.; Tafti, S. A.; Kim, H. Y.; Choi, S. Y.; Downey, K. J.; Nguyen, T. V. J. Org. Chem. 2001, 66, 7191-7194.
10. See for examples: (a) Okimoto, M.; Chiba, T. Synthesis 1996, 1188-1190. (b) Poirier, D.; Berthiaume, D.; Boivin, R. P. Synlett 1999, 1423-1425. (c) Berthiaume, D.; Poirier, D. Tetrahedron 2000, 56, 5995-6003. (d) Deardorff, D. R.; Taniguchi, C. M.; Tafti, S. A.; Kim, H. Y.; Choi, S. Y.; Downey, K. J.; Nguyen, T. V. J. Org. Chem. 2001, 66, 7191-7194.
11. See for examples: (a) Okimoto, M.; Chiba, T. Synthesis 1996, 1188-1190. (b) Poirier, D.; Berthiaume, D.; Boivin, R. P. Synlett 1999, 1423-1425. (c) Berthiaume, D.; Poirier, D. Tetrahedron 2000, 56, 5995-6003. (d) Deardorff, D. R.; Taniguchi, C. M.; Tafti, S. A.; Kim, H. Y.; Choi, S. Y.; Downey, K. J.; Nguyen, T. V. J. Org. Chem. 2001, 66, 7191-7194.
12. Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195-6.
13. (a) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636-8.
14. (b) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2003, 5, 3021-4.
15. Casas, J.; Baeza, A.; Sansano, J. M.; Nájera, C.; Saá, J. M. Tetrahedron: Asymmetry 2003, 14, 197-200.
16. All enantiomeric excesses were determined by chiral GLC and are accurate to ±3%.
17. 3) for (R)-enantiomer with 94% ee]; δH 1.26 (3H, t J 7.2), 4.21 (2H, q J 7.2), 6.19 (1H, s), 7.2-7.5 (5H, m).
18. Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636-3638. 4507