Synthesis of a Tertiary Carbinamide via a Novel Rh-Catalyzed Asymmetric Hydrogenation.
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| Title: | Synthesis of a Tertiary Carbinamide via a Novel Rh-Catalyzed Asymmetric Hydrogenation. |
|---|---|
| Authors: | Limanto, John1 john_limanto@merck.com, Shultz, C. Scott1, Dorner, Benjamin1, Desmond, Richard A.1, Devine, Paul N.1, Krska, Shane W.1 |
| Source: | Journal of Organic Chemistry. 2/15/2008, Vol. 73 Issue 4, p1639-1642. 4p. 4 Charts. |
| Subjects: | Amides, Organic synthesis, Catalysis, Hydrogenation, Rhodium compounds, Metal complexes, Crystallization |
| Abstract: | Asymmetric hydrogenation of allylic dimethylcarbinamide 2 with 1 mol % of cationic Rh(I)—Josiphos complex in THF under 500 psi of H2 generated the corresponding tertiary carbinamide 1 in 98.5% assay yield and a 94:6 enantiomeric ratio. Upon crystallization, the product was isolated in 91% isolated yield and 95:5 enantiomeric ratio. [ABSTRACT FROM AUTHOR] |
| Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 31124422 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Synthesis of a Tertiary Carbinamide via a Novel Rh-Catalyzed Asymmetric Hydrogenation. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Limanto%2C+John%22">Limanto, John</searchLink><relatesTo>1</relatesTo><i> john_limanto@merck.com</i><br /><searchLink fieldCode="AR" term="%22Shultz%2C+C%2E+Scott%22">Shultz, C. Scott</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Dorner%2C+Benjamin%22">Dorner, Benjamin</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Desmond%2C+Richard+A%2E%22">Desmond, Richard A.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Devine%2C+Paul+N%2E%22">Devine, Paul N.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Krska%2C+Shane+W%2E%22">Krska, Shane W.</searchLink><relatesTo>1</relatesTo> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 2/15/2008, Vol. 73 Issue 4, p1639-1642. 4p. 4 Charts. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Amides%22">Amides</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+synthesis%22">Organic synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Catalysis%22">Catalysis</searchLink><br /><searchLink fieldCode="DE" term="%22Hydrogenation%22">Hydrogenation</searchLink><br /><searchLink fieldCode="DE" term="%22Rhodium+compounds%22">Rhodium compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Metal+complexes%22">Metal complexes</searchLink><br /><searchLink fieldCode="DE" term="%22Crystallization%22">Crystallization</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: Asymmetric hydrogenation of allylic dimethylcarbinamide 2 with 1 mol % of cationic Rh(I)—Josiphos complex in THF under 500 psi of H2 generated the corresponding tertiary carbinamide 1 in 98.5% assay yield and a 94:6 enantiomeric ratio. Upon crystallization, the product was isolated in 91% isolated yield and 95:5 enantiomeric ratio. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1021/jo702429u Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 4 StartPage: 1639 Subjects: – SubjectFull: Amides Type: general – SubjectFull: Organic synthesis Type: general – SubjectFull: Catalysis Type: general – SubjectFull: Hydrogenation Type: general – SubjectFull: Rhodium compounds Type: general – SubjectFull: Metal complexes Type: general – SubjectFull: Crystallization Type: general Titles: – TitleFull: Synthesis of a Tertiary Carbinamide via a Novel Rh-Catalyzed Asymmetric Hydrogenation. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Limanto, John – PersonEntity: Name: NameFull: Shultz, C. Scott – PersonEntity: Name: NameFull: Dorner, Benjamin – PersonEntity: Name: NameFull: Desmond, Richard A. – PersonEntity: Name: NameFull: Devine, Paul N. – PersonEntity: Name: NameFull: Krska, Shane W. IsPartOfRelationships: – BibEntity: Dates: – D: 15 M: 02 Text: 2/15/2008 Type: published Y: 2008 Identifiers: – Type: issn-print Value: 00223263 Numbering: – Type: volume Value: 73 – Type: issue Value: 4 Titles: – TitleFull: Journal of Organic Chemistry Type: main |
| ResultId | 1 |
