1-(2,4,6-Triisopropylphenyl)ethylamine: A New Chiral Auxiliary for the Asymmetric Synthesis of γ-Amino Acid Derivatives.
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| Title: | 1-(2,4,6-Triisopropylphenyl)ethylamine: A New Chiral Auxiliary for the Asymmetric Synthesis of γ-Amino Acid Derivatives. |
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| Authors: | Cividino, Pascale1, Py, Sandrine1 sandrine.py@ujf-grenoble.fr, Delair, Philippe1, Greene, Andrew E.1 andrew.greene@ujf-grenoble.fr |
| Source: | Journal of Organic Chemistry. 1/19/2007, Vol. 72 Issue 2, p485-493. 9p. 3 Charts. |
| Subjects: | Ethylamines, Asymmetric synthesis, Amino acids, Aldehydes, Chemical reactions, Organic chemistry |
| Abstract: | The title compound has proven to be an excellent chiral auxiliary for nitrones in SmI2-mediated reductive coupling with α,β-unsaturated esters. A variety of such nitrones, prepared from aldehydes and enantiopure N-hydroxy-1-(2,4,6-triisopropylphenyl)ethylamine, afforded γ-N-hydroxyamino esters in high yields and diastereomeric purity. These adducts, readily available as either enantiomer, could be transformed into γ-N-acetoxyamino esters, N-Boc-γ-amino esters, and γ-lactams. [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: 23764002 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: 1-(2,4,6-Triisopropylphenyl)ethylamine: A New Chiral Auxiliary for the Asymmetric Synthesis of γ-Amino Acid Derivatives. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Cividino%2C+Pascale%22">Cividino, Pascale</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Py%2C+Sandrine%22">Py, Sandrine</searchLink><relatesTo>1</relatesTo><i> sandrine.py@ujf-grenoble.fr</i><br /><searchLink fieldCode="AR" term="%22Delair%2C+Philippe%22">Delair, Philippe</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Greene%2C+Andrew+E%2E%22">Greene, Andrew E.</searchLink><relatesTo>1</relatesTo><i> andrew.greene@ujf-grenoble.fr</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 1/19/2007, Vol. 72 Issue 2, p485-493. 9p. 3 Charts. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Ethylamines%22">Ethylamines</searchLink><br /><searchLink fieldCode="DE" term="%22Asymmetric+synthesis%22">Asymmetric synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Amino+acids%22">Amino acids</searchLink><br /><searchLink fieldCode="DE" term="%22Aldehydes%22">Aldehydes</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+reactions%22">Chemical reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+chemistry%22">Organic chemistry</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: The title compound has proven to be an excellent chiral auxiliary for nitrones in SmI2-mediated reductive coupling with α,β-unsaturated esters. A variety of such nitrones, prepared from aldehydes and enantiopure N-hydroxy-1-(2,4,6-triisopropylphenyl)ethylamine, afforded γ-N-hydroxyamino esters in high yields and diastereomeric purity. These adducts, readily available as either enantiomer, could be transformed into γ-N-acetoxyamino esters, N-Boc-γ-amino esters, and γ-lactams. [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/jo061976i Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 9 StartPage: 485 Subjects: – SubjectFull: Ethylamines Type: general – SubjectFull: Asymmetric synthesis Type: general – SubjectFull: Amino acids Type: general – SubjectFull: Aldehydes Type: general – SubjectFull: Chemical reactions Type: general – SubjectFull: Organic chemistry Type: general Titles: – TitleFull: 1-(2,4,6-Triisopropylphenyl)ethylamine: A New Chiral Auxiliary for the Asymmetric Synthesis of γ-Amino Acid Derivatives. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Cividino, Pascale – PersonEntity: Name: NameFull: Py, Sandrine – PersonEntity: Name: NameFull: Delair, Philippe – PersonEntity: Name: NameFull: Greene, Andrew E. IsPartOfRelationships: – BibEntity: Dates: – D: 19 M: 01 Text: 1/19/2007 Type: published Y: 2007 Identifiers: – Type: issn-print Value: 00223263 Numbering: – Type: volume Value: 72 – Type: issue Value: 2 Titles: – TitleFull: Journal of Organic Chemistry Type: main |
| ResultId | 1 |
