First practical method for asymmetric epoxidation

Details First practical method for asymmetric epoxidation First practical method for asymmetric epoxidation

B - Operations, Transporting

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252/111, 260/370

B01J 31/38 (2006.01) C07D 301/00 (2006.01) C07D 301/19 (2006.01) C07D 303/04 (2006.01) C07D 303/14 (2006.01) C07D 303/48 (2006.01)

Patent

CA 1168219

ABSTRACT OF THE DISCLOSURE Methods and compositions are provided for asymecrically 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. Greatly enhanced yields of enantiomers are achieved as compared to prior enantioselective introduction of oxygen. This invention was made at least in part in the course of a grant from the U.S. National Institutes of Health (GM24551).

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