Claims
- 1. 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).
- 2. 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.
- 3. The method of claim 2, wherein the step of reducing said intermediate is carried out at room temperature in a reaction mixture additionally comprising sodium borohydride in a 1:1 mixture of isopropyl alcohol and tetrahydrofuran.
- 4. The method of claim 2, wherein the step of separating the compound of Formula I from its diastereoisomer is carried out by column chromatography.
- 5. The method of claim 2, comprising the additional steps, following the step of reducing said intermediate and preceding the step of separating said compound from the reaction mixture and its diastereoisomer, of:
(i) quenching the reaction mixture; and (ii) recovering said compound.
- 6. 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).
- 7. The method of claim 6, wherein said metal-alkyl donor compound is dialkylzinc.
- 8. The method of claim 7, wherein said metal-alkyl donor compound is diethylzinc.
- 9. The method of claim 6, wherein said starting ketone compound is of Formula II:
- 10. The method of claim 9, wherein said starting ketone compound is a straight or branched C1-C9 alkyl ketone, a straight or branched C1-C9 alkyl aryl ketone, or a straight or branched C1-C9 α, β-unsaturated ketone which is optionally substituted with Ar.
- 11. The method of claim 6, wherein said method comprises the additional step of isolating the resulting chiral tertiary alcohol.
Parent Case Info
[0001] This application claims the benefit of U.S. Provisional Patent Application No. 60/364,883, filed Mar. 14, 2003, the contents of which is hereby incorporated by reference in its entirety.
[0002] This work was supported in part by National Institutes of Health grant GM58101 and by National Science Foundation grant CHE-9733274. The United States government may have rights in this invention by virtue of this support.
Provisional Applications (1)
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Number |
Date |
Country |
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60364883 |
Mar 2002 |
US |