Practical asymmetric synthesis of β-trichloromethyl-β-hydroxy ketones by the reaction of chloral or chloral hydrate with chiral imines

Organic Letters

Volumn 5, Issue 12, 2003, Pages 2059-2061

  Funabiki, Kazumasa ^a   Honma, Norihiro ^a   Hashimoto, Wataru ^a   Matsui, Masaki ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORAL; CHLORAL HYDRATE; IMINE; KETONE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; CRYSTALLIZATION; ENANTIOSELECTIVITY; HYDROLYSIS; REACTION ANALYSIS;

CHLORAL HYDRATE; CRYSTALLIZATION; DRUG DESIGN; HYDROCARBONS, CHLORINATED; HYDROXYLATION; IMINES; KETONES; SOLVENTS; STEREOISOMERISM; TECHNOLOGY, PHARMACEUTICAL;

EID: 0141519517     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034461b     Document Type: Article

References (15)

1. Corey, E. J.; Link, John O. Tetrahedron Lett. 1992, 33, 3431.
2. (a) Corey, E. J.; Link, J. O. J. Am. Chem. Soc. 1992, 114, 1906.
3. (b) Mellin-Morliere, C.; Aitken, D. J.; Bull, S. D.; Davies, S. G.; Husson, H.-P. Tetrahedron: Asymmetry 2001, 12, 149.
4. (c) Tennyson, R. L.; Cortez, G. S.; Galicia, H. J.; Kreiman, C. R.; Thompson, C. M.; Romo, D. Org. Lett. 2002, 4, 533.
5. Khrimian, A. P.; Oliver, J. E.; Waters, R. M.; Panicker, S.; Nicholson, J. M.; Klun, J. A. Tetrahedron: Asymmetry 1996, 7, 37.
6. Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1993, 34, 5227.
7. Fujisawa, T.; Ito, T.; Fujimoto, K.; Shimizu, M.; Wynberg, H.; Staring, E. G. J. Tetrahedron Lett. 1997, 38, 1593.
8. For another recent example, see. Huffman, M. A.; Reider, P. J. Tetrahedron Lett. 1999, 40, 831.
9. Fujisawa, T.; Ito, T.; Nishiura, S.; Shimizu, M. Tetrahedron Lett. 1998, 39, 9735.
10. Shimizu, M.; Ishii, K.; Fujisawa, T. Chem. Lett. 1997, 765.
11. For the reaction of chloral with achiral enamine leading to the racemic β-trichloro-β-hydroxy aldehyde, see: Brannock, K. C.; Burpitt, H. E.; Davis, H. E.; Pridgen, H. S.; Thweatt, J. B. J. Org. Chem. 1967, 29, 2579.
12. (a) Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P. J. Org. Chem. 2001, 66, 256.
13. (b) Arend, M.; Risch, N. Angew. Chem., Int. Ed. 1995, 34, 2639.
14. (c) Pfau, M.; Revaial, G.; Guingant, A.; d'Angelo, J. J. Am. Chem. Soc. 1985, 107, 273.
15. Ishii, A.; Kanai, M.; Higashiyama, K.; Mikami, K. Chirality 2002, 14, 709.