Nucleophilic Carbene Catalyzed Synthesis of 1,2 Amino Alcohols Via Azidation of Epoxy Aldehydes.
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| Title: | Nucleophilic Carbene Catalyzed Synthesis of 1,2 Amino Alcohols Via Azidation of Epoxy Aldehydes. |
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| Authors: | Vora, Harit U.1, Moncecchi, Johannah R.1, Epstein, Oleg1, Rovis, Tomislav1 rovis@lamar.colostate.edu |
| Source: | Journal of Organic Chemistry. 12/19/2008, Vol. 73 Issue 24, p9727-9731. 5p. 2 Charts. |
| Subjects: | Organic chemistry, Chemical reactions, Aldehydes, Nucleophilic reactions, Amino acids, Nitrogen compounds |
| Abstract: | We report herein a nucleophilic carbene catalyzed redox azidation of epoxyaldehydes. The intermediate β-hydroxy acyl azides undergo thermal Curtius rearrangement followed by trapping with excess azide to form carbamoyl azides or, in a complementary sequence, by the hydroxy group to form oxazolidinones. Both products are formed in modest to good yields and diastereoselectivities. The use of an enantioenriched triazolium catalyst leads to modest asymmetric induction. [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: 35919244 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Nucleophilic Carbene Catalyzed Synthesis of 1,2 Amino Alcohols Via Azidation of Epoxy Aldehydes. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Vora%2C+Harit+U%2E%22">Vora, Harit U.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Moncecchi%2C+Johannah+R%2E%22">Moncecchi, Johannah R.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Epstein%2C+Oleg%22">Epstein, Oleg</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Rovis%2C+Tomislav%22">Rovis, Tomislav</searchLink><relatesTo>1</relatesTo><i> rovis@lamar.colostate.edu</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 12/19/2008, Vol. 73 Issue 24, p9727-9731. 5p. 2 Charts. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Organic+chemistry%22">Organic chemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+reactions%22">Chemical reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Aldehydes%22">Aldehydes</searchLink><br /><searchLink fieldCode="DE" term="%22Nucleophilic+reactions%22">Nucleophilic reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Amino+acids%22">Amino acids</searchLink><br /><searchLink fieldCode="DE" term="%22Nitrogen+compounds%22">Nitrogen compounds</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: We report herein a nucleophilic carbene catalyzed redox azidation of epoxyaldehydes. The intermediate β-hydroxy acyl azides undergo thermal Curtius rearrangement followed by trapping with excess azide to form carbamoyl azides or, in a complementary sequence, by the hydroxy group to form oxazolidinones. Both products are formed in modest to good yields and diastereoselectivities. The use of an enantioenriched triazolium catalyst leads to modest asymmetric induction. [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/jo8020055 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 5 StartPage: 9727 Subjects: – SubjectFull: Organic chemistry Type: general – SubjectFull: Chemical reactions Type: general – SubjectFull: Aldehydes Type: general – SubjectFull: Nucleophilic reactions Type: general – SubjectFull: Amino acids Type: general – SubjectFull: Nitrogen compounds Type: general Titles: – TitleFull: Nucleophilic Carbene Catalyzed Synthesis of 1,2 Amino Alcohols Via Azidation of Epoxy Aldehydes. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Vora, Harit U. – PersonEntity: Name: NameFull: Moncecchi, Johannah R. – PersonEntity: Name: NameFull: Epstein, Oleg – PersonEntity: Name: NameFull: Rovis, Tomislav IsPartOfRelationships: – BibEntity: Dates: – D: 19 M: 12 Text: 12/19/2008 Type: published Y: 2008 Identifiers: – Type: issn-print Value: 00223263 Numbering: – Type: volume Value: 73 – Type: issue Value: 24 Titles: – TitleFull: Journal of Organic Chemistry Type: main |
| ResultId | 1 |
