Chiral lithium binaphtholate aqua complex as a highly effective asymmetric catalyst for cyanohydrin synthesis

Journal of the American Chemical Society

Volumn 127, Issue 31, 2005, Pages 10776-10777

  Hatano, Manabu ^a   Ikeno, Takumi ^a   Miyamoto, Takashi ^a   Ishihara, Kazuaki ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYANOHYDRIN; LEWIS ACID; LITHIUM DERIVATIVE; NAPHTHOL DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; COMPLEX FORMATION; CYANATION; ENANTIOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; SYNTHESIS;

EID: 23744496756     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051125c     Document Type: Article

References (28)

1. For reviews, see: (a) North, M. Synlett 1993, 807-820.
2. (b) Effenberger, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1555-1564.
3. (c) North, M. Tetrahedron: Asymmetry 2003, 14, 147-176.
4. (d) Brunel, J.-M.; Holmes, I. P. Angew. Chem., Int. Ed. 2004, 43, 2752-2778.
5. (a) Norsikian, S.; Holmes, I.; Lagasse, F.; Kagan, H. B. Tetrahedron Lett. 2002, 43, 5715-5717.
6. (b) Belokon, Y. N.; North, M.; Maleev, V. I.; Voskoboev, N. V.; Moskalenko, M. A.; Peregudov, A. S.; Dmitriev, A. V.; Ikonnikov, N. S.; Kagan, H. B. Angew. Chem., Int. Ed. 2004, 43, 4085-4089.
7. Lewis base catalysis with ketones. (a) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195-6196.
8. (b) Tian, S.-K.; Hong, R.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900-9901.
9. (c) Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; Medaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621-631.
10. (a) Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001-4004.
11. (b) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8106-8107.
12. (c) Huang, J.; Corey, E. J. Org. Lett. 2004, 6, 5027-5029.
13. Recent intensive reports; (a) Belokon, Y. N.; Blacker, A. J.; Carta, P.; Clutterbuck, L. A.; North, M. Tetrahedron 2004, 60, 10433-10477.
14. (b) Yamagiwa, N.; Tian, J.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 3413-3422.
15. Gregory, R. J. H. Chem. Rev. 1999, 99, 3649-3682.
16. (a) Holmes, I. P.; Kagan, H. B. Tetrahedron Lett. 2000, 41, 7453-7456.
17. (b) Holmes, I. P.; Kagan, H. B. Tetrahedron Lett. 2000, 41, 7457-7460.
18. Our following experiments consisted of Kagan's report, especially from the viewpoint of stereochemistry of cyanohydrin. See ref 7a.
19. During the course of the reaction and the workup procedure, no racemization or kinetic resolution occurred in the presence or absence of chiral catalyst, using isolated enantiomerically enriched or racemic cyanohydrin, trimethylsilyl ether, and corresponding acetate.
20. Recently, the enantioselective aldol reaction catalyzed by (R)-2 with excess water to activate Si atom was reported. Nakajima, M.; Orito, Y.; Ishizuka, T.; Hashimoto, S. Org. Lett. 2004, 6, 3763-3765.
21. TMSCN/i-PrOH (1:1) in toluene at 0 °C for 2 h was treated to prepare HCN. Mai, K.; Patil, G. J. Org. Chem. 1986, 51, 3545-3548.
22. LiOAc-catalyzed aldol reaction. Nakagawa, T.; Fujisawa, H.; Mukaiyama, T. Chem. Lett. 2003, 32, 462-463.
23. For X-ray crystallographic structures of polymeric (A)-1 and (A)-2, see: (a) Toda, F.; Tanaka, K.; Wong, M. C.; Mak, T. C. W. Chem. Lett. 1987, 2069-2072.
24. (b) Aspinall, H. C.; Bickley, J. F.; Dwyer, J. L. M.; Greeves, N.; Steiner, A. Angew. Chem., Int. Ed. 2000, 39, 2858-2861.
25. n < (R)-1·i-PrOH ≪ dry (R)-1 < dry (R)-2.
26. (a) Hosomi, A.; Hayashida, H.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1986, 1411-1412.
27. (b) Kohra, S.; Hayashida, H.; Tominaga, Y.; Hosomi, A. Tetrahedron Lett. 1988, 44, 89-92.
28. (c) Hayashi, T.; Matsumoto, Y.; Kiyoi, T.; Ito, Y.; Kohra, S.; Tominaga, Y.; Hosomi, A. Tetrahedron Lett. 1988, 44, 5667-5670.