Process for preparation of optically active halogeno...

Details Process for preparation of optically active halogeno... Process for preparation of optically active halogeno...

2005-09-20

2005-09-20

Dentz, Bernard (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C568S674000, C568S811000, C568S844000, C560S105000, C560S111000, C560S236000

Reexamination Certificate

active

06946566

ABSTRACT:
A process for preparing regioselectively an optically active 1-halogeno-2-hydroxypropyl compound of the following formula;wherein X is halogen atom and Nu is a heteroatom having a substituent,and an optically active glycidyl compound of the formula;which comprises reacting an optically active epihalohydrin of the formula;with a neucleophilic agent,in the presence of a metal complex of the formula;wherein n is an integer of 0, 1 or 2, Y1, Y2and Y3are hydrogen atom, etc., and Y2and Y3may form a ring such as benzene, A is a counterion and M is a metal ion, and further subjecting the compound (4) to reaction with a base to prepare the optically active glycidyl compound (5).

REFERENCES:
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Takano et al., “Practical Preparation of Optically Active O-0 Benzylglycidol From Optically Active Epichlorohydrin”, Heterocycles, vol. 31, No. 9, pp. 1715-1719 (1990).
Schaus et al., “Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral salen)CoIIIComplexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-Diols”, J. Am. Chem. Soc., vol. 124, No. 7 pp. 1307-1315 (2002).
Chemical Abstracts, vol. 114, No. 19, May 13, 1991, Columbus, Ohio, U.S.; abstract No. 185001, Takano Seiichi et al: “Preparation of optically-active 2-hydroxy-3-hydrocarbyloxypropyl halides or sulfonates”, XP002257262 & JP 02 286643 A (Daiso Co., Ltd., Japan), Nov. 26, 1990.

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