Phenolytic Kinetic Resolution of Azido and Alkoxy Epoxides

A single step process for the synthesis of α-Aryloxy-α′-Azido/Alkoxy alcohols of general formula A with two stereocenters by phenolic kinetic resolution,

• wherein X is selected from N3 and OBn;
• ‘R’ is selected independently from hydrogen, alkyl (C1-C5), alkenyls (C2-C6), alkynyls (C2-C6), aryl, alkoxy, cyano, halo, nitro, —C(O)—R1, —CO2R2, hydroxyl, —NH(R3), cycloalkyl, cycloalkenyl, thiols, thiocarbonyl, sulfonyl or a heterocycle(C3-C5), where R1, R2 and R3 represent hydrogen, alkyl(C1-C5).
• Y denotes TBSO or phenyl;
• and
• ‘a’ and ‘b’ denote syn or anti position
• Wherein the said process comprising the steps of:
• (a) adding racemic epoxide of formula (1),
• to phenol of formula (2)
• wherein, X, Y and R are as defined above,
• at room temperature ranging between 25-35° C. to preformed (salen) Co (III) catalyst of formula 3,
• followed by addition of tertiary butyl methyl ether, stirring and adding pyridinium p-toluene sulfonate, filtering, concentrating, followed by purifying to obtain the α-Aryloxy-α′-Azido/Alkoxy alcohols of general formula A