Samarium Iodide-Mediated Reformatsky Reactions for the Stereoselective Preparation of β-Hydroxy-γ-amino Acids: Synthesis of Isostatine and Dolaisoleucine.
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| Title: | Samarium Iodide-Mediated Reformatsky Reactions for the Stereoselective Preparation of β-Hydroxy-γ-amino Acids: Synthesis of Isostatine and Dolaisoleucine. |
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| Authors: | Nelson, Christopher G.1, Burke Jr., Terrence R.1 tburke@helix.nih.gov |
| Source: | Journal of Organic Chemistry. 1/6/2012, Vol. 77 Issue 1, p733-738. 6p. |
| Subjects: | Samarium iodide, Stereoselective reactions, Hydroxy acids, Amino acids, Organic synthesis |
| Abstract: | The synthesis of β-hydroxy-γ-amino acids via SmI2-mediated Reformatsky reactions of α-chloroacetyloxazolidinones with aminoaldehydes is reported. Diastereoselective coupling is demonstrated to depend on the absolute configuration of the Evans chiral auxiliary employed in the reaction, allowing erythro or threo products to be obtained selectively. The potential utility of the methodology is exemplified by the facile synthesis of biologically relevant N-Boc-isostatine (2b) and N-Boc-dolaisoleucine (3c). [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: 70504025 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Samarium Iodide-Mediated Reformatsky Reactions for the Stereoselective Preparation of β-Hydroxy-γ-amino Acids: Synthesis of Isostatine and Dolaisoleucine. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Nelson%2C+Christopher+G%2E%22">Nelson, Christopher G.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Burke+Jr%2E%2C+Terrence+R%2E%22">Burke Jr., Terrence R.</searchLink><relatesTo>1</relatesTo><i> tburke@helix.nih.gov</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 1/6/2012, Vol. 77 Issue 1, p733-738. 6p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Samarium+iodide%22">Samarium iodide</searchLink><br /><searchLink fieldCode="DE" term="%22Stereoselective+reactions%22">Stereoselective reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Hydroxy+acids%22">Hydroxy acids</searchLink><br /><searchLink fieldCode="DE" term="%22Amino+acids%22">Amino acids</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+synthesis%22">Organic synthesis</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: The synthesis of β-hydroxy-γ-amino acids via SmI2-mediated Reformatsky reactions of α-chloroacetyloxazolidinones with aminoaldehydes is reported. Diastereoselective coupling is demonstrated to depend on the absolute configuration of the Evans chiral auxiliary employed in the reaction, allowing erythro or threo products to be obtained selectively. The potential utility of the methodology is exemplified by the facile synthesis of biologically relevant N-Boc-isostatine (2b) and N-Boc-dolaisoleucine (3c). [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/jo202091r Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 6 StartPage: 733 Subjects: – SubjectFull: Samarium iodide Type: general – SubjectFull: Stereoselective reactions Type: general – SubjectFull: Hydroxy acids Type: general – SubjectFull: Amino acids Type: general – SubjectFull: Organic synthesis Type: general Titles: – TitleFull: Samarium Iodide-Mediated Reformatsky Reactions for the Stereoselective Preparation of β-Hydroxy-γ-amino Acids: Synthesis of Isostatine and Dolaisoleucine. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Nelson, Christopher G. – PersonEntity: Name: NameFull: Burke Jr., Terrence R. IsPartOfRelationships: – BibEntity: Dates: – D: 06 M: 01 Text: 1/6/2012 Type: published Y: 2012 Identifiers: – Type: issn-print Value: 00223263 Numbering: – Type: volume Value: 77 – Type: issue Value: 1 Titles: – TitleFull: Journal of Organic Chemistry Type: main |
| ResultId | 1 |
