Patent ID: 6686483
Filing Date: 2004-02-03
Classification: C07B,C07C,C07D,C07F,C07H

Abstract:
A method of producing an epoxide from an olefin comprising:contacting an oxidizing agent with an olefin in the presence of a chiral ketone under conditions sufficient to produce an epoxide from the olefin, wherein the chiral ketone is selected from the group consisting of a compound of the formula: â€ƒor a derivative thereof which is capable of converting to the chiral ketone of Formula I under the reaction conditions, wherein bonds a and b are of cis-configuration relative to each other; n is 0 or 1; X is selected from the group consisting of O and CR7R8, where R7 and R8 is independently selected from the group consisting of hydrogen, alkyl, haloalkyl and heteroalkyl, or R7 together with R4 together with the atoms to which they are attached to form an optionally substituted heterocyclyl; each of R1 and R2 is independently selected from the group consisting of hydrogen or alkyl, or R1 and R2 together with atoms to which they are attached to form a cycloalkyl; R3 is selected from the group consisting of hydrogen and OR9, where R9 is a hydroxyl protecting group or aryl group; R5 is alkylene; R4 is hydrogen or a hydroxy protecting group; and R6 is hydrogen, alkyl, or â€”ORa, where Ra is hydrogen or a hydroxy protecting group; or R4 and R6 together with the atoms to which they are attached to form an optionally substituted heterocyclyl.