Cinchona-based bifunctional organocatalysts and method for preparing chiral hemiesters using the same
AssigneeSungkyunkwan University Foundation for Corporate Collaboration
InventorsChoong Eui SONG, Sang Ho OH, Ho Sik RHO, Ji Woong LEE, Je Wun LEE, Sung Hoon YOUK, Jik CHIN
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Abstract
The present invention relates to cinchona-based bifunctional organocatalysts and methods for preparing chiral hemiesters using the same. More specifically, the present invention relates to methods for preparing chiral hemiesters from prochiral or meso cyclic acid anhydrides via desymmetrization, using bifunctional cinchona alkaloid catalysts comprising sulfonamide functional groups.
Claims21
A compound of Formula 1 or 2 and its salt:
- wherein,
- Ar represents an aryl having 4 to 11 member ring,
- R2, R3, R4, R6, R7 and R8 represent hydrogen,
- R5 represent an alkyl having 1 to 12 carbons, an alkenyl having 2 to 12 carbons, an alkynyl having 2 to 12 carbons, an alkoxy having 1 to 12 carbons or an aryl having 4 to 11 member ring, and
- Y represents an alkyl having 1 to 12 carbons, an alkenyl having 2 to 12 carbons, a cycloalkyl having 3 to 10 carbons, or an aryl having 4 to 11 member ring, with the proviso that Y is not para-toluene.
- wherein,
- Ar represents an aryl having 4 to 11 member ring,
- R2, R4, R5, R6, R7 and R8 represent hydrogen,
- R3 represent an alkyl having 1 to 12 carbons, an alkenyl having 2 to 12 carbons, an alkynyl having 2 to 12 carbons, an alkoxy having 1 to 12 carbons or an aryl having 4 to 11 member ring, and
- Y represents an alkyl having 1 to 12 carbons, an alkenyl having 2 to 12 carbons, a cycloalkyl having 3 to 10 carbons, or an aryl having 4 to 11 member ring, with the proviso that Y is not para-toluene.
A method for preparing a chiral hemiester comprising a step of reacting a prochiral compound or a meso-cyclic acid anhydride with a nucleophile in the presence of a compound of Formula I below:
- wherein,
- X represents an organic group containing 1-azabicyclo[2.2.2]octane moiety;
- and
- Y represents alkyl, alkenyl, cycloalkyl, or aryl.
Dependencies are inferred from the claim text.