Commercialization of the hydrolytic kinetic resolution of racemic epoxides: Toward the economical large-scale production of enantiopure epichlorohydrin

Tetrahedron Asymmetry

Volumn 14, Issue 22, 2003, Pages 3589-3592

  Larrow, Jay F ^a   Hemberger, Karl E ^a   Jasmin, Serge ^a   Kabir, Hocine ^b   Morel, Phillipe ^b  

^a Rhodia Pharma Solutions   (United States)

^b Rhodia Europe   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ASCORBIC ACID; EPICHLOROHYDRIN; EPOXIDE;

ARTICLE; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; HYDROLYSIS; PRIORITY JOURNAL; REDUCTION;

EID: 0242541816     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.09.018     Document Type: Article

References (9)

1. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938. For a comprehensive review of asymmetric processes catalysed by chiral (salen)metal complexes, see: Larrow, J. F.; Jacobsen, E. N. In Topics in Organometallic Chemistry; Larsen, R. D., Ed.; Springer-Verlag: Heidelberg, in press.
2. Schaus S.E., Brandes B.D., Larrow J.F., Tokunaga M., Hansen K.B., Gould A.E., Furrow M.E., Jacobsen E.N. J. Am. Chem. Soc. 124:2002;1307-1315.
3. Furrow M.E., Schaus S.E., Jacobsen E.N. J. Org. Chem. 63:1998;6776-6777.
4. Aouni, L.; Hemberger, K. E.; Jasmin, S.; Kabir, H.; Larrow, J. F.; Le-Fur, I.; Morel, P.; Schlama, T. Industrialization Studies of the Jacobsen Hydrolytic Kinetic Resolution of Epichlorohydrin. In Asymmetric Catalysis on Industrial Scale; Blaser, H.-U.; Schmidt, E., Eds.; Wiley-VCH: Weinheim, in press.
5. Schaus S.E., Jacobsen E.N. Tetrahedron Lett. 37:1996;7937-7940.
6. Takeichi T., Ishimori M., Tsuruta T. Bull. Chem. Soc. Jpn. 52:1979;2614-2618.
7. Takeichi T., Arihara M., Ishimori M., Tsuruta T. Tetrahedron. 36:1980;3391-3398.
8. For further scale-up, more exact hazard evaluation experiments indicated that the pot temperature should not exceed 70°C.
9. The rate of water addition (and hence the rate of reaction) is balanced to the rate of heat transfer out of the vessel in order to maintain a reaction temperature of about 5°C. In this experiment, the jacket temperature was maintained near -5°C (ΔT=10°C).