Assembly of Indoline-2-carboxylate-Embodied Dipeptides via Pd-Catalyzed C(sp2)–H Bond Direct Functionalization
Intramolecular dehydrogenative cyclization of 2-methoxyiminoacyl-protected phenylalanine derivatives proceeded at 110 °C under catalysis of Pd(OAc)2 in the presence of 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate to afford substituted indoline-2-carboxylates that were converted into indoline...
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| Published in | Organic letters Vol. 17; no. 3; pp. 496 - 499 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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06.02.2015
Amer Chemical Soc |
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| Abstract | Intramolecular dehydrogenative cyclization of 2-methoxyiminoacyl-protected phenylalanine derivatives proceeded at 110 °C under catalysis of Pd(OAc)2 in the presence of 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate to afford substituted indoline-2-carboxylates that were converted into indoline-2-carboxylate-embodied dipeptides via Raney Ni-catalyzed hydrogenation. |
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| AbstractList | Intramolecular dehydrogenative cyclization of 2-methoxyiminoacyl-protected phenylalanine derivatives proceeded at 110 °C under catalysis of Pd(OAc)₂ in the presence of 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate to afford substituted indoline-2-carboxylates that were converted into indoline-2-carboxylate-embodied dipeptides via Raney Ni-catalyzed hydrogenation. Intramolecular dehydrogenative cyclization of 2-methoxyiminoacyl-protected phenylalanine derivatives proceeded at 110 degrees C under catalysis of Pd(OAc)(2) in the presence of 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate to afford substituted indoline-2-carboxylates that were converted into indoline-2-carboxylate-embodied dipeptides via Raney Ni-catalyzed hydrogenation. Intramolecular dehydrogenative cyclization of 2-methoxyiminoacyl-protected phenylalanine derivatives proceeded at 110 °C under catalysis of Pd(OAc)2 in the presence of 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate to afford substituted indoline-2-carboxylates that were converted into indoline-2-carboxylate-embodied dipeptides via Raney Ni-catalyzed hydrogenation. Intramolecular dehydrogenative cyclization of 2-methoxyiminoacyl-protected phenylalanine derivatives proceeded at 110 °C under catalysis of Pd(OAc)2 in the presence of 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate to afford substituted indoline-2-carboxylates that were converted into indoline-2-carboxylate-embodied dipeptides via Raney Ni-catalyzed hydrogenation.Intramolecular dehydrogenative cyclization of 2-methoxyiminoacyl-protected phenylalanine derivatives proceeded at 110 °C under catalysis of Pd(OAc)2 in the presence of 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate to afford substituted indoline-2-carboxylates that were converted into indoline-2-carboxylate-embodied dipeptides via Raney Ni-catalyzed hydrogenation. |
| Author | He, Yu-Peng Wu, Zhijie Zhang, Chao Ma, Dawei Fan, Mengyang |
| AuthorAffiliation | Chinese Academy of Sciences College of Chemistry, Chemical Engineering and Environmental Engineering Liaoning Shihua University State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry |
| AuthorAffiliation_xml | – name: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry – name: College of Chemistry, Chemical Engineering and Environmental Engineering – name: Chinese Academy of Sciences – name: Liaoning Shihua University |
| Author_xml | – sequence: 1 givenname: Yu-Peng surname: He fullname: He, Yu-Peng – sequence: 2 givenname: Chao surname: Zhang fullname: Zhang, Chao – sequence: 3 givenname: Mengyang surname: Fan fullname: Fan, Mengyang – sequence: 4 givenname: Zhijie surname: Wu fullname: Wu, Zhijie – sequence: 5 givenname: Dawei surname: Ma fullname: Ma, Dawei email: madw@mail.sioc.ac.cn |
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| Keywords | PALLADIUM FLUORIDE ACTIVATION DIRECT ARYLATION ACETOXYLATION INDOLINE COMPLEXES REDUCTIVE ELIMINATION DERIVATIVES PD(II)-CATALYZED AMINATION METALLOPROTEASE INHIBITORS |
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| SubjectTerms | Carboxylic Acids - chemical synthesis Carboxylic Acids - chemistry Catalysis catalytic activity chemical structure Chemistry Chemistry, Organic Cyclization dipeptides Dipeptides - chemical synthesis Dipeptides - chemistry Hydrogenation Indoles - chemical synthesis Indoles - chemistry Molecular Structure organic compounds palladium Palladium - chemistry phenylalanine Physical Sciences Science & Technology |
| Title | Assembly of Indoline-2-carboxylate-Embodied Dipeptides via Pd-Catalyzed C(sp2)–H Bond Direct Functionalization |
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