Patent ID: 6552226
Filing Date: 2003-04-22
Classification: C07D

Abstract:
A method for conducting a tandem Claisen rearrangement reaction, comprising reacting an allylic reactant with at least one acid chloride in the presence of a Lewis acid catalyst composition comprising a first catalyst component composed of a Lewis acid, and a second catalyst component selected from the group consisting of tertiary amines and non-nitrogenous bases, wherein the allylic reactant is seminally di-substituted with a first substitute â€”C(R4R5)â€”Z1Q1(Q2)m and a second substituent â€”C(R6R7)â€”Z2Q3(Q4)u, wherein:R4, R5, R6, and R7 are independently selected from the group consisting of hybrido, halo, hydroxyl, sulfhydryl, amino, substituted amino, hydrocarbyl, substituted hydrocarbyl, heteroatoms-containing hydrocarbyl, and substituted heteroatom-containing hydrocarbyl; Z1 and Z2 are independently N, O or S; m is zero or 1, with the proviso that when Z1 is N, m is 1, and when Z1 is S or O, m is zero; n is zero or 1, with the further proviso that when Z2 is N, n is 1, and when Z2 is S or O, n is zero; and Q1, Q2, Q3 and Q4 are independently selected from the group consisting of hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatoms-containing hydrocarbyl, or, when Z1 is N and m is 1, Q1 and Q2 are joined together in a ring structure or together with Z1 form an azide group, or, when Z2 is N and n is 1, Q3 and Q4 are joined together in a ring structure or together with Z2 form an azide group, and further wherein the molar ratio of acid chloride to the allylic reactant is selected to enable the reactant to undergo at least two successive Claisen rearrangement reactions.