Method for asymmetric epoxidation

Details Method for asymmetric epoxidation Method for asymmetric epoxidation

1981-07-27

1984-09-11

Brown, Johnnie R.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

260429R, 2604295, 536124, 536127, 536 72, 560218, 562402, 562401, 568902, 568913, C07C 4504

Patent

active

044711301

ABSTRACT:
Methods and compositions are provided for asymmetrically donating an oxygen atom to a pair of electrons to produce an asymmetric product. Specifically, a metal alkoxide is used as a catalyst, where the metal has a coordination number of at least four, and at least one, usually two, of the alkoxide groups bonded to the metal are bonded to asymmetric carbon atoms. The metal catalyst is employed in conjunction with a hydroperoxide and an alkanol having a functionality with a pair of electrons capable of accepting an oxygen atom. The resulting product is enriched in one enantiomer due to the enantioselective introduction of an asymmetric center or an enhanced rate of reaction of one of the enantiomers of a chiral alkanol.

REFERENCES:
patent: 2867577 (1959-01-01), Urban, Jr. et al.
patent: 3436409 (1969-04-01), Hill et al.
patent: 3935272 (1976-01-01), Chapurlat
Yamada et al., "Jour. Amer. Chem. Soc.", vol. 99, Mar. 1977, pp. 1988-1990.
Michaelson et al., "Jour. Amer. Chem. Soc.", vol. 99, Mar. 1977, pp. 1990-1992.
Tani et al., "Tetrahedron Letters", vol. 32, pp. 3017-3020, 1979.

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