Room-temperature enantioselective C–H iodination via kinetic resolution
Asymmetric carbon-hydrogen (C–H) activation reactions often rely on desymmetrization of prochiral C–H bonds on the same achiral molecule, using a chiral catalyst. Here, we report a kinetic resolution via palladium-catalyzed enantioselective C–H iodination in which one of the enantiomers of a racemic...
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| Published in | Science (American Association for the Advancement of Science) Vol. 346; no. 6208; pp. 451 - 455 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Association for the Advancement of Science
24.10.2014
The American Association for the Advancement of Science |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Asymmetric carbon-hydrogen (C–H) activation reactions often rely on desymmetrization of prochiral C–H bonds on the same achiral molecule, using a chiral catalyst. Here, we report a kinetic resolution via palladium-catalyzed enantioselective C–H iodination in which one of the enantiomers of a racemic benzylic amine substrates undergoes faster aryl C–H insertion with the chiral catalysts than the other. The resulting enantioenriched C–H functionalization products would not be accessible through desymmetrization of prochiral C–H bonds. The exceedingly high relative rate ratio (k
fast/k
slow up to 244), coupled with the subsequent iodination of the remaining enantiomerically enriched starting material using a chiral ligand with the opposite configuration, enables conversion of both substrate enantiomers into enantiomerically pure iodinated products. |
|---|---|
| AbstractList | Asymmetric carbon-hydrogen (C-H) activation reactions often rely on desymmetrization of prochiral C-H bonds on the same achiral molecule, using a chiral catalyst. Here, we report a kinetic resolution via palladium-catalyzed enantioselective C-H iodination in which one of the enantiomers of a racemic benzylic amine substrates undergoes faster aryl C-H insertion with the chiral catalysts than the other. The resulting enantioenriched C-H functionalization products would not be accessible through desymmetrization of prochiral C-H bonds. The exceedingly high relative rate ratio (k(fast)/k(slow) up to 244), coupled with the subsequent iodination of the remaining enantiomerically enriched starting material using a chiral ligand with the opposite configuration, enables conversion of both substrate enantiomers into enantiomerically pure iodinated products.Asymmetric carbon-hydrogen (C-H) activation reactions often rely on desymmetrization of prochiral C-H bonds on the same achiral molecule, using a chiral catalyst. Here, we report a kinetic resolution via palladium-catalyzed enantioselective C-H iodination in which one of the enantiomers of a racemic benzylic amine substrates undergoes faster aryl C-H insertion with the chiral catalysts than the other. The resulting enantioenriched C-H functionalization products would not be accessible through desymmetrization of prochiral C-H bonds. The exceedingly high relative rate ratio (k(fast)/k(slow) up to 244), coupled with the subsequent iodination of the remaining enantiomerically enriched starting material using a chiral ligand with the opposite configuration, enables conversion of both substrate enantiomers into enantiomerically pure iodinated products. Ensuring handedness when breaking C-H bonds Many organic compounds are chiral: They manifest two distinct mirror-image variants, or enantiomers. Kinetic resolution can transform one enantiomer to a desired product while leaving its mirror image unmodified. Chu et al. applied this strategy to a reaction that replaces aryl carbon–hydrogen bonds with carbon-iodine bonds. They used a chiral palladium catalyst that reacts selectively with just one of two enantiomers of various benzylamine derivatives. In medicinal chemistry, such selective synthesis of individual enantiomers is essential for screening interactions with chiral biomolecules such as proteins. Science , this issue p. 451 Many organic compounds are chiral: They manifest two distinct mirror-image variants, or enantiomers. Kinetic resolution can transform one enantiomer to a desired product while leaving its mirror image unmodified. Chu et al. applied this strategy to a reaction that replaces aryl carbon-hydrogen bonds with carbon-iodine bonds. They used a chiral palladium catalyst that reacts selectively with just one of two enantiomers of various benzylamine derivatives. In medicinal chemistry, such selective synthesis of individual enantiomers is essential for screening interactions with chiral biomolecules such as proteins. Science, this issue p. 451 Asymmetric carbon-hydrogen (C-H) activation reactions often rely on desymmetrization of prochiral C-H bonds on the same achiral molecule, using a chiral catalyst. Here, we report a kinetic resolution via palladium-catalyzed enantioselective C-H iodination in which one of the enantiomers of a racemic benzylic amine substrates undergoes faster aryl C-H insertion with the chiral catalysts than the other. The resulting enantioenriched C-H functionalization products would not be accessible through desymmetrization of prochiral C-H bonds. The exceedingly high relative rate ratio (kfast/kslow up to 244), coupled with the subsequent iodination of the remaining enantiomerically enriched starting material using a chiral ligand with the opposite configuration, enables conversion of both substrate enantiomers into enantiomerically pure iodinated products. Asymmetric carbon-hydrogen (C-H) activation reactions often rely on desymmetrization of prochiral C-H bonds on the same achiral molecule, using a chiral catalyst. Here, we report a kinetic resolution via palladium-catalyzed enantioselective C-H iodination in which one of the enantiomers of a racemic benzylic amine substrates undergoes faster aryl C-H insertion with the chiral catalysts than the other. The resulting enantioenriched C-H functionalization products would not be accessible through desymmetrization of prochiral C-H bonds. The exceedingly high relative rate ratio (k(fast)/k(slow) up to 244), coupled with the subsequent iodination of the remaining enantiomerically enriched starting material using a chiral ligand with the opposite configuration, enables conversion of both substrate enantiomers into enantiomerically pure iodinated products. Ensuring handedness when breaking C-H bondsMany organic compounds are chiral: They manifest two distinct mirror-image variants, or enantiomers. Kinetic resolution can transform one enantiomer to a desired product while leaving its mirror image unmodified. Chu et al. applied this strategy to a reaction that replaces aryl carbon-hydrogen bonds with carbon-iodine bonds. They used a chiral palladium catalyst that reacts selectively with just one of two enantiomers of various benzylamine derivatives. In medicinal chemistry, such selective synthesis of individual enantiomers is essential for screening interactions with chiral biomolecules such as proteins.Science, this issue p. 451 Asymmetric carbon-hydrogen (C-H) activation reactions often rely on desymmetrization of prochiral C-H bonds on the same achiral molecule, using a chiral catalyst. Here, we report a kinetic resolution via palladium-catalyzed enantioselective C-H iodination in which one of the enantiomers of a racemic benzylic amine substrates undergoes faster aryl C-H insertion with the chiral catalysts than the other. The resulting enantioenriched C-H functionalization products would not be accessible through desymmetrization of prochiral C-H bonds. The exceedingly high relative rate ratio (kfast/kslow up to 244), coupled with the subsequent iodination of the remaining enantiomerically enriched starting material using a chiral ligand with the opposite configuration, enables conversion of both substrate enantiomers into enantiomerically pure iodinated products. Many organic compounds are chiral: They manifest two distinct mirror-image variants, or enantiomers. Kinetic resolution can transform one enantiomer to a desired product while leaving its mirror image unmodified. Chu et al. applied this strategy to a reaction that replaces aryl carbon–hydrogen bonds with carbon-iodine bonds. They used a chiral palladium catalyst that reacts selectively with just one of two enantiomers of various benzylamine derivatives. In medicinal chemistry, such selective synthesis of individual enantiomers is essential for screening interactions with chiral biomolecules such as proteins. Science , this issue p. 451 Palladium catalysis produces benzylamine derivatives of interest in medicinal chemistry. Asymmetric carbon-hydrogen (C–H) activation reactions often rely on desymmetrization of prochiral C–H bonds on the same achiral molecule, using a chiral catalyst. Here, we report a kinetic resolution via palladium-catalyzed enantioselective C–H iodination in which one of the enantiomers of a racemic benzylic amine substrates undergoes faster aryl C–H insertion with the chiral catalysts than the other. The resulting enantioenriched C–H functionalization products would not be accessible through desymmetrization of prochiral C–H bonds. The exceedingly high relative rate ratio ( k fast / k slow up to 244), coupled with the subsequent iodination of the remaining enantiomerically enriched starting material using a chiral ligand with the opposite configuration, enables conversion of both substrate enantiomers into enantiomerically pure iodinated products. Asymmetric carbon-hydrogen (C–H) activation reactions often rely on desymmetrization of prochiral C–H bonds on the same achiral molecule, using a chiral catalyst. Here, we report a kinetic resolution via palladium-catalyzed enantioselective C–H iodination in which one of the enantiomers of a racemic benzylic amine substrates undergoes faster aryl C–H insertion with the chiral catalysts than the other. The resulting enantioenriched C–H functionalization products would not be accessible through desymmetrization of prochiral C–H bonds. The exceedingly high relative rate ratio (k fast/k slow up to 244), coupled with the subsequent iodination of the remaining enantiomerically enriched starting material using a chiral ligand with the opposite configuration, enables conversion of both substrate enantiomers into enantiomerically pure iodinated products. The development of asymmetric C–H activation reactions through metal insertions remains in its infancy. The commonly used approach is the desymmetrization of prochiral C–H bonds on the same or different carbons of one achiral molecule using a chiral catalyst. Herein, we report a Pd-catalyzed enantioselective C–H activation reaction via kinetic resolution in which one of the enantiomers of the racemic substrates undergoes faster C–H insertion with the chiral catalysts thereby producing enantioenriched C–H functionalization products that are not accessible via desymmtrization of prochiral C–H bonds. The exceedingly high relative rate ( k fast / k slow up to 244) and the subsequent iodination of the remaining enantiomerically enriched starting material using a chiral ligand with the opposite configuration allows for the conversion of both enantiomers of amines into enantiomerically pure iodinated amines. |
| Author | Xiao, Kai-Jiong Chu, Ling Yu, Jin-Quan |
| Author_xml | – sequence: 1 givenname: Ling surname: Chu fullname: Chu, Ling – sequence: 2 givenname: Kai-Jiong surname: Xiao fullname: Xiao, Kai-Jiong – sequence: 3 givenname: Jin-Quan surname: Yu fullname: Yu, Jin-Quan |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25342799$$D View this record in MEDLINE/PubMed |
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| CODEN | SCIEAS |
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| ContentType | Journal Article |
| Copyright | Copyright © 2014 American Association for the Advancement of Science Copyright © 2014, American Association for the Advancement of Science. Copyright © 2014, American Association for the Advancement of Science |
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| DOI | 10.1126/science.1258538 |
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| Snippet | Asymmetric carbon-hydrogen (C–H) activation reactions often rely on desymmetrization of prochiral C–H bonds on the same achiral molecule, using a chiral... Many organic compounds are chiral: They manifest two distinct mirror-image variants, or enantiomers. Kinetic resolution can transform one enantiomer to a... Asymmetric carbon-hydrogen (C-H) activation reactions often rely on desymmetrization of prochiral C-H bonds on the same achiral molecule, using a chiral... Ensuring handedness when breaking C-H bondsMany organic compounds are chiral: They manifest two distinct mirror-image variants, or enantiomers. Kinetic... Ensuring handedness when breaking C-H bonds Many organic compounds are chiral: They manifest two distinct mirror-image variants, or enantiomers. Kinetic... The development of asymmetric C–H activation reactions through metal insertions remains in its infancy. The commonly used approach is the desymmetrization of... |
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| SubjectTerms | ambient temperature Aromatic compounds Asymmetry Carbon Catalysis Catalysts chemical bonding Chemical bonds Enantiomers Enzyme kinetics Hydrogen bonds Iodination Iodine Kinetics Organic Chemistry Organic compounds Palladium Proteins Reaction kinetics screening Substrates |
| Title | Room-temperature enantioselective C–H iodination via kinetic resolution |
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