Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions
The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η4-diene complex with Fe(CO)3) in a short sequence of steps: 1) nucleophilic amine addition and subsequent Boc-protection, 2) photochemical demetallation of the iron com...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2023-10-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.19.118 |
| _version_ | 1797632993918976000 |
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| author | Aaron H. Shoemaker Elizabeth A. Foker Elena P. Uttaro Sarah K. Beitel Daniel R. Griffith |
| author_facet | Aaron H. Shoemaker Elizabeth A. Foker Elena P. Uttaro Sarah K. Beitel Daniel R. Griffith |
| author_sort | Aaron H. Shoemaker |
| collection | DOAJ |
| description | The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η4-diene complex with Fe(CO)3) in a short sequence of steps: 1) nucleophilic amine addition and subsequent Boc-protection, 2) photochemical demetallation of the iron complex, and 3) an intramolecular Heck reaction. Minor modifications to the protocol enabled access to the related 2-azabicyclo[4.4.1]undecane system, albeit in lower yield. |
| first_indexed | 2024-03-11T11:44:32Z |
| format | Article |
| id | doaj.art-5421ed867b3a4fc0b1f4452930873b55 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-03-11T11:44:32Z |
| publishDate | 2023-10-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-5421ed867b3a4fc0b1f4452930873b552023-11-09T15:03:35ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972023-10-011911615161910.3762/bjoc.19.1181860-5397-19-118Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactionsAaron H. Shoemaker0Elizabeth A. Foker1Elena P. Uttaro2Sarah K. Beitel3Daniel R. Griffith4Department of Chemistry, Lafayette College, 730 High St., Easton, PA 18042, USA Department of Chemistry, Lafayette College, 730 High St., Easton, PA 18042, USA Department of Chemistry, Lafayette College, 730 High St., Easton, PA 18042, USA Department of Chemistry, Lafayette College, 730 High St., Easton, PA 18042, USA Department of Chemistry, Lafayette College, 730 High St., Easton, PA 18042, USA The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η4-diene complex with Fe(CO)3) in a short sequence of steps: 1) nucleophilic amine addition and subsequent Boc-protection, 2) photochemical demetallation of the iron complex, and 3) an intramolecular Heck reaction. Minor modifications to the protocol enabled access to the related 2-azabicyclo[4.4.1]undecane system, albeit in lower yield.https://doi.org/10.3762/bjoc.19.118alkaloidsazabicyclesheck reactioniron complextropone |
| spellingShingle | Aaron H. Shoemaker Elizabeth A. Foker Elena P. Uttaro Sarah K. Beitel Daniel R. Griffith Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions Beilstein Journal of Organic Chemistry alkaloids azabicycles heck reaction iron complex tropone |
| title | Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions |
| title_full | Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions |
| title_fullStr | Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions |
| title_full_unstemmed | Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions |
| title_short | Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions |
| title_sort | synthesis of 7 azabicyclo 4 3 1 decane ring systems from tricarbonyl tropone iron via intramolecular heck reactions |
| topic | alkaloids azabicycles heck reaction iron complex tropone |
| url | https://doi.org/10.3762/bjoc.19.118 |
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