π-Face selective azaspirocyclization of ω-(methoxyphenyl)-N-methoxyalkylamides
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| Title: | π-Face selective azaspirocyclization of ω-(methoxyphenyl)-N-methoxyalkylamides |
|---|---|
| Authors: | Wardrop, Duncan J. wardropd@uic.edu, Burge, Matthew S.1, Zhang, Wenming1, Ortız, José A.1 |
| Source: | Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Mar2003, Vol. 44 Issue 12, p2587. 5p. |
| Subjects: | Ring formation (Chemistry), Organic synthesis |
| Abstract: | A novel method for the stereoselective preparation of 1-azaspiranes is described. Treatment of α- and β-substituted 3-(methoxyphenyl)-N-methoxypropionamides 1 with phenyliodine(III) bis(trifluoroacetate) initiates efficient azaspirocyclization, via a putative N-acylnitrenium ion intermediate, to provide cyclohexa-2,5 and 2,4-dienone spirolactams 8 and 11 with good π-facial selectivity. Furthermore, a preliminary study indicates that this strategy is also amenable to the preparation of 1-azaspiro[5.5]undeca-2,5-dienones. [Copyright &y& Elsevier] |
| Copyright of Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry is the property of Pergamon Press - An Imprint of Elsevier Science 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: 9189413 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: π-Face selective azaspirocyclization of ω-(methoxyphenyl)-N-methoxyalkylamides – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Wardrop%2C+Duncan+J%2E%22">Wardrop, Duncan J.</searchLink><i> wardropd@uic.edu</i><br /><searchLink fieldCode="AR" term="%22Burge%2C+Matthew+S%2E%22">Burge, Matthew S.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Zhang%2C+Wenming%22">Zhang, Wenming</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Ortız%2C+José+A%2E%22">Ortız, José A.</searchLink><relatesTo>1</relatesTo> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Tetrahedron+Letters%3A+International+Organ+for+the+Rapid+Publication+of+Preliminary+Communications+in+Organic+Chemistry%22">Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry</searchLink>. Mar2003, Vol. 44 Issue 12, p2587. 5p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Ring+formation+%28Chemistry%29%22">Ring formation (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+synthesis%22">Organic synthesis</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: A novel method for the stereoselective preparation of 1-azaspiranes is described. Treatment of α- and β-substituted 3-(methoxyphenyl)-N-methoxypropionamides 1 with phenyliodine(III) bis(trifluoroacetate) initiates efficient azaspirocyclization, via a putative N-acylnitrenium ion intermediate, to provide cyclohexa-2,5 and 2,4-dienone spirolactams 8 and 11 with good π-facial selectivity. Furthermore, a preliminary study indicates that this strategy is also amenable to the preparation of 1-azaspiro[5.5]undeca-2,5-dienones. [Copyright &y& Elsevier] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry is the property of Pergamon Press - An Imprint of Elsevier Science 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: 10.1016/S0040-4039(03)00227-2 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 5 StartPage: 2587 Subjects: – SubjectFull: Ring formation (Chemistry) Type: general – SubjectFull: Organic synthesis Type: general Titles: – TitleFull: π-Face selective azaspirocyclization of ω-(methoxyphenyl)-N-methoxyalkylamides Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Wardrop, Duncan J. – PersonEntity: Name: NameFull: Burge, Matthew S. – PersonEntity: Name: NameFull: Zhang, Wenming – PersonEntity: Name: NameFull: Ortız, José A. IsPartOfRelationships: – BibEntity: Dates: – D: 17 M: 03 Text: Mar2003 Type: published Y: 2003 Identifiers: – Type: issn-print Value: 00404039 Numbering: – Type: volume Value: 44 – Type: issue Value: 12 Titles: – TitleFull: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry Type: main |
| ResultId | 1 |
