Application of the Curtius rearrangement to the synthesis of 1′-aminoferrocene-1-carboxylic acid derivatives
The shortest synthesis of N -protected 1′-aminoferrocene-1-carboxylic acid from readily available ferrocene-1,1′-dicarboxylic acid is reported. 1′-Azidocarbonylferrocene-1-carboxylic acid was first obtained by reaction of the latter with diphenylphosphoryl azide. It was then converted into four amin...
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| Veröffentlicht in: | New journal of chemistry 2018, Vol.42 (5), p.388-3818 |
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| container_title | New journal of chemistry |
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| creator | Erb, William Levanen, Gael Roisnel, Thierry Dorcet, Vincent |
| description | The shortest synthesis of
N
-protected 1′-aminoferrocene-1-carboxylic acid from readily available ferrocene-1,1′-dicarboxylic acid is reported. 1′-Azidocarbonylferrocene-1-carboxylic acid was first obtained by reaction of the latter with diphenylphosphoryl azide. It was then converted into four amino acids by a Curtius rearrangement conducted in the presence of
tert
-butanol, benzyl alcohol, 9-fluorenemethanol or allyl alcohol. The benzyl and allyl carbamate derivatives are reported and characterized for the first time. The four corresponding new succinimidyl activated esters were also prepared and their usefulness was demonstrated in peptide coupling. Various structures were elucidated by X-ray crystallography, including 1′-azidocarbonylferrocene-1-carboxylic acid and 1,1′-diazidocarbonylferrocene.
The shortest synthesis of
N
-protected 1′-aminoferrocene-1-carboxylic acid from readily available ferrocene-1,1′-dicarboxylic acid is reported. |
| doi_str_mv | 10.1039/c7nj05020h |
| format | Article |
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N
-protected 1′-aminoferrocene-1-carboxylic acid from readily available ferrocene-1,1′-dicarboxylic acid is reported. 1′-Azidocarbonylferrocene-1-carboxylic acid was first obtained by reaction of the latter with diphenylphosphoryl azide. It was then converted into four amino acids by a Curtius rearrangement conducted in the presence of
tert
-butanol, benzyl alcohol, 9-fluorenemethanol or allyl alcohol. The benzyl and allyl carbamate derivatives are reported and characterized for the first time. The four corresponding new succinimidyl activated esters were also prepared and their usefulness was demonstrated in peptide coupling. Various structures were elucidated by X-ray crystallography, including 1′-azidocarbonylferrocene-1-carboxylic acid and 1,1′-diazidocarbonylferrocene.
The shortest synthesis of
N
-protected 1′-aminoferrocene-1-carboxylic acid from readily available ferrocene-1,1′-dicarboxylic acid is reported.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/c7nj05020h</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Alcohol ; Amino acids ; Benzyl alcohol ; Butanol ; Chemical Sciences ; Crystallography ; Derivatives ; Esters ; Synthesis</subject><ispartof>New journal of chemistry, 2018, Vol.42 (5), p.388-3818</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c351t-aa391c08713ccab76d11b1615c0081dfbfbe4e261577b61973d03c71e59c4faf3</citedby><cites>FETCH-LOGICAL-c351t-aa391c08713ccab76d11b1615c0081dfbfbe4e261577b61973d03c71e59c4faf3</cites><orcidid>0000-0002-2906-2091 ; 0000-0002-6088-4472</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://univ-rennes.hal.science/hal-01740157$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Erb, William</creatorcontrib><creatorcontrib>Levanen, Gael</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><creatorcontrib>Dorcet, Vincent</creatorcontrib><title>Application of the Curtius rearrangement to the synthesis of 1′-aminoferrocene-1-carboxylic acid derivatives</title><title>New journal of chemistry</title><description>The shortest synthesis of
N
-protected 1′-aminoferrocene-1-carboxylic acid from readily available ferrocene-1,1′-dicarboxylic acid is reported. 1′-Azidocarbonylferrocene-1-carboxylic acid was first obtained by reaction of the latter with diphenylphosphoryl azide. It was then converted into four amino acids by a Curtius rearrangement conducted in the presence of
tert
-butanol, benzyl alcohol, 9-fluorenemethanol or allyl alcohol. The benzyl and allyl carbamate derivatives are reported and characterized for the first time. The four corresponding new succinimidyl activated esters were also prepared and their usefulness was demonstrated in peptide coupling. Various structures were elucidated by X-ray crystallography, including 1′-azidocarbonylferrocene-1-carboxylic acid and 1,1′-diazidocarbonylferrocene.
The shortest synthesis of
N
-protected 1′-aminoferrocene-1-carboxylic acid from readily available ferrocene-1,1′-dicarboxylic acid is reported.</description><subject>Alcohol</subject><subject>Amino acids</subject><subject>Benzyl alcohol</subject><subject>Butanol</subject><subject>Chemical Sciences</subject><subject>Crystallography</subject><subject>Derivatives</subject><subject>Esters</subject><subject>Synthesis</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpFkbFOwzAQhi0EEqWwsCNFYgLJ4IuTuBmrCiioggVmy3Fs6qq1g51UdOOZeCSeBLdBZTrr_N1_v38jdA7kBggtbyWzC5KTlMwP0ABoUeIyLeAwniHLMMmz4hidhLAgBIAVMEB23DRLI0VrnE2cTtq5Siadb00XEq-E98K-q5WybdK63WXY2FiCCVsafr6-sVgZ67Ty3kllFQYsha_c5ybKJkKaOqmVN-u4Ya3CKTrSYhnU2V8dorf7u9fJFM9eHh4n4xmWNIcWC0FLkGTEgEopKlbUABUUkEtCRlDrSlcqU_FlOWNVASWjNaGSgcpLmWmh6RBd9bpzseSNNyvhN9wJw6fjGd_2CLCMxPE1RPayZxvvPjoVWr5wnbfRHk8JRBNpFrMdouuekt6F4JXeywLh2-z5hD0_7bKfRviih32Qe-7_b-gvjQeB3g</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Erb, William</creator><creator>Levanen, Gael</creator><creator>Roisnel, Thierry</creator><creator>Dorcet, Vincent</creator><general>Royal Society of Chemistry</general><general>Royal Society of Chemistry [1987-....]</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-2906-2091</orcidid><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid></search><sort><creationdate>2018</creationdate><title>Application of the Curtius rearrangement to the synthesis of 1′-aminoferrocene-1-carboxylic acid derivatives</title><author>Erb, William ; Levanen, Gael ; Roisnel, Thierry ; Dorcet, Vincent</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c351t-aa391c08713ccab76d11b1615c0081dfbfbe4e261577b61973d03c71e59c4faf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alcohol</topic><topic>Amino acids</topic><topic>Benzyl alcohol</topic><topic>Butanol</topic><topic>Chemical Sciences</topic><topic>Crystallography</topic><topic>Derivatives</topic><topic>Esters</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Erb, William</creatorcontrib><creatorcontrib>Levanen, Gael</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><creatorcontrib>Dorcet, Vincent</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Erb, William</au><au>Levanen, Gael</au><au>Roisnel, Thierry</au><au>Dorcet, Vincent</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Application of the Curtius rearrangement to the synthesis of 1′-aminoferrocene-1-carboxylic acid derivatives</atitle><jtitle>New journal of chemistry</jtitle><date>2018</date><risdate>2018</risdate><volume>42</volume><issue>5</issue><spage>388</spage><epage>3818</epage><pages>388-3818</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>The shortest synthesis of
N
-protected 1′-aminoferrocene-1-carboxylic acid from readily available ferrocene-1,1′-dicarboxylic acid is reported. 1′-Azidocarbonylferrocene-1-carboxylic acid was first obtained by reaction of the latter with diphenylphosphoryl azide. It was then converted into four amino acids by a Curtius rearrangement conducted in the presence of
tert
-butanol, benzyl alcohol, 9-fluorenemethanol or allyl alcohol. The benzyl and allyl carbamate derivatives are reported and characterized for the first time. The four corresponding new succinimidyl activated esters were also prepared and their usefulness was demonstrated in peptide coupling. Various structures were elucidated by X-ray crystallography, including 1′-azidocarbonylferrocene-1-carboxylic acid and 1,1′-diazidocarbonylferrocene.
The shortest synthesis of
N
-protected 1′-aminoferrocene-1-carboxylic acid from readily available ferrocene-1,1′-dicarboxylic acid is reported.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/c7nj05020h</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-2906-2091</orcidid><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2018, Vol.42 (5), p.388-3818 |
| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_01740157v1 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alcohol Amino acids Benzyl alcohol Butanol Chemical Sciences Crystallography Derivatives Esters Synthesis |
| title | Application of the Curtius rearrangement to the synthesis of 1′-aminoferrocene-1-carboxylic acid derivatives |
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