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US 2003/0191345 A1Published application
Catalysts, methods for making said catalysts, and methods for making chiral compounds with high enantioselectivity
AssigneeThe Trustees of the University of Pennsylvania
InventorPatrick J. Walsh
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Abstract
The present invention relates to compounds useful as catalysts in asymmetric synthesis of chiral compounds, methods for the synthesis of said catalysts, and methods for synthesizing chiral compounds with high enantioselectivity.
Drawings
Claims11
A compound selected from the group consisting of:
- Bicyclo[2.2.1]heptane-1-methanesulfonamide,N,N′-(1S,2S)-1,2-cyclohexanediylbis[2-hydroxy-7,7-dimethyl]-(1R,1′R,2S,2′S,4S,4′S)-(9CI) and Bicyclo[2.2.1]heptane-1-methanesulfonamide,N,N′-(1R,2R)-1,2-cyclohexanediylbis[2-hydroxy-7,7-dimethyl]-(1S,1′S,2R,2′R,4R,4′R)-(9CI).
A method for making a compound selected from the group consisting of:
- Bicyclo[2.2.1]heptane-1-methanesulfonamide,N,N′-(1S,2S)-1,2-cyclohexanediylbis[2-hydroxy-7,7-dimethyl]-(1R,1′R,2S,2′S,4S,4′S)-(9CI) and Bicyclo[2.2.1]heptane-1-methanesulfonamide,N,N′-(1R,2R)-1,2-cyclohexanediylbis[2-hydroxy-7,7-dimethyl]-(1S,1′S,2R,2′R,4R,4′R)-(9CI), comprising the steps of:
- (a) reducing an enantiomer of 1,2-bis(camphorsulfonamido)-cyclohexane;
- and
- (b) separating said compound from the reaction mixture and its diastereoisomer.
1 more element
A method for making a chiral tertiary alcohol with high enantioselectivity, comprising reacting a metal-alkyl donor compound with a starting ketone compound in the presence of titanium(IV) isopropoxide and a compound selected from the group consisting of:
- Bicyclo[2.2.l]heptane-1-methanesulfonamide,N,N′-(1S,2S)-1,2-cyclohexanediylbis[2-hydroxy-7,7-dimethyl]-(1R,1′R,2S,2′S,4S,4′S)-(9CI) and Bicyclo[2.2.1]heptane-1-methanesulfonamide,N,N′-(1R,2R)-1,2-cyclohexanediylbis[2-hydroxy-7,7-dimethyl]-(1S,1′S,2R,2′R,4R,4′R)-(9CI).
Dependencies are inferred from the claim text.