PROCESSES FOR PRODUCING 'alpha'-HALO KETONES, 'alpha'-HALOHYDRINS AND EPOXIDES

WIPO Patent Application WO/1996/023756

A1

Processes for efficiently producing 'alpha'-halo ketones, 'alpha'-halohydrins and epoxides on an industrial scale. The processes include one for producing an 'alpha'-halo ketone of general formula (3) by decarboxylating a product of reaction between a carboxylic acid derivative of general formula (1) and a metal enolate prepared from an 'alpha'-haloacetic acid of general formula (2) or an acceptable salt thereof, one for producing an 'alpha'-halohydrin (11) by reducing the 'alpha'-halo ketone (3), and one for producing an epoxide (13) by treating the 'alpha'-halohydrin (11) with a base to effect ring closure. The above processes are particularly suitable for producing optically active 'alpha'-halo ketones, 'alpha'-halohydrins and epoxides from the corresponding 'alpha'-amino acid derivatives.

NISHIYAMA AKIRA (JP)
SUGAWA TADASHI (JP)
MANABE HAJIME (JP)
INOUE KENJI (JP)
YOSHIDA NORITAKA (JP)

PCT/JP1996/000212

August 08, 1996

February 02, 1996

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KANEKA CORP (JP)
NISHIYAMA AKIRA (JP)
SUGAWA TADASHI (JP)
MANABE HAJIME (JP)
INOUE KENJI (JP)
YOSHIDA NORITAKA (JP)

C07C29/143; C07C45/48; C07C269/06; C07C319/20; C07D303/36; C07C323/43; (IPC1-7): C07C45/48; C07C29/143; C07C33/46; C07C49/80; C07C213/00; C07C215/28; C07C221/00; C07C225/16; C07D301/26; C07D303/04; C07D303/36

TETRAHEDRON, Vol. 50, No. 21 (1994), A. ALBECK et al., "Stereocontrolled Synthesis of Erythro N-Protected alpha-Amino Epoxides and Peptidyl Epoxides", pp. 6333-6346.
See also references of EP 0754669A4

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