Convenient synthesis of chiral tryptophan derivatives using Negishi cross-coupling
A facile synthetic procedure for chiral tryptophan derivatives using Negishi cross-coupling reaction of serine-derived iodoalanine with 3-haloindole is described. The best result was obtained when the reaction of N-tosyl-3-bromoindole with N-Cbz-iodoalanine methyl ester was carried out by the combin...
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| Veröffentlicht in: | Tetrahedron 2011-08, Vol.67 (33), p.5897-5901 |
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| container_title | Tetrahedron |
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| creator | Tanaka, Minoru Hikawa, Hidemasa Yokoyama, Yuusaku |
| description | A facile synthetic procedure for chiral tryptophan derivatives using Negishi cross-coupling reaction of serine-derived iodoalanine with 3-haloindole is described. The best result was obtained when the reaction of
N-tosyl-3-bromoindole with
N-Cbz-iodoalanine methyl ester was carried out by the combination of Pd
2(dba)
3 and sterically hindered ferrocenyl ligand Q-PHOS. This reaction condition not only gave the desired tryptophan derivative as high as 76% yield, but also suppressed the formation of undesired products, the dehalogenated indole and the homodimer of indole, which were difficult to separate. This reaction was extended to the synthesis of various tryptophan derivatives having substituents on the benzene ring. The characteristic of this reaction is the practical biomimetic synthesis of chiral tryptophan derivatives in one-step.
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| doi_str_mv | 10.1016/j.tet.2011.06.053 |
| format | Article |
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N-tosyl-3-bromoindole with
N-Cbz-iodoalanine methyl ester was carried out by the combination of Pd
2(dba)
3 and sterically hindered ferrocenyl ligand Q-PHOS. This reaction condition not only gave the desired tryptophan derivative as high as 76% yield, but also suppressed the formation of undesired products, the dehalogenated indole and the homodimer of indole, which were difficult to separate. This reaction was extended to the synthesis of various tryptophan derivatives having substituents on the benzene ring. The characteristic of this reaction is the practical biomimetic synthesis of chiral tryptophan derivatives in one-step.
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N-tosyl-3-bromoindole with
N-Cbz-iodoalanine methyl ester was carried out by the combination of Pd
2(dba)
3 and sterically hindered ferrocenyl ligand Q-PHOS. This reaction condition not only gave the desired tryptophan derivative as high as 76% yield, but also suppressed the formation of undesired products, the dehalogenated indole and the homodimer of indole, which were difficult to separate. This reaction was extended to the synthesis of various tryptophan derivatives having substituents on the benzene ring. The characteristic of this reaction is the practical biomimetic synthesis of chiral tryptophan derivatives in one-step.
[Display omitted]</description><subject>Biomimetic synthesis</subject><subject>Biomimetics</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Derivatives</subject><subject>Esters</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Indoles</subject><subject>Ligands</subject><subject>Negishi cross-coupling</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Synthesis (chemistry)</subject><subject>Tryptophan</subject><subject>Unusual amino acids</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9kE9Lw0AQxRdRsFY_gLdcBC-Js5vNhuBJiv-gKIiel81m0m5Jk7izLfTbu7XFo6dhhvfezPwYu-aQceDqbpUFDJkAzjNQGRT5CZtwqWRaSK5O2QRAQipBwDm7IFoBRKXIJ-xjNvRb7B32IaFdH5ZIjpKhTezSedMlwe_GMIxL0ycNerc1wW2Rkg25fpG84cLR0iXWD0SpHTZjF8eX7Kw1HeHVsU7Z19Pj5-wlnb8_v84e5qmVQoUUedOYUjRQ5SAVNLlSQtlKtghoZAtFWVRQq9zUNaimLmsbm7aorZA5WlPlU3Z7yB398L1BCnrtyGLXmR6HDWleSqliSCmjlB-kv5d6bPXo3dr4neag9_z0Skd-es9Pg9KRX_TcHOMNWdO13vTW0Z9RyEJWgu-z7w86jL9uHXpNNuK02DiPNuhmcP9s-QGZ84cb</recordid><startdate>20110819</startdate><enddate>20110819</enddate><creator>Tanaka, Minoru</creator><creator>Hikawa, Hidemasa</creator><creator>Yokoyama, Yuusaku</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20110819</creationdate><title>Convenient synthesis of chiral tryptophan derivatives using Negishi cross-coupling</title><author>Tanaka, Minoru ; Hikawa, Hidemasa ; Yokoyama, Yuusaku</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c426t-e1dda72d0930460d36626c94fe0ea4f057590b63abb06db7bcb63f5bc243eca93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Biomimetic synthesis</topic><topic>Biomimetics</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Derivatives</topic><topic>Esters</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Indoles</topic><topic>Ligands</topic><topic>Negishi cross-coupling</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Synthesis (chemistry)</topic><topic>Tryptophan</topic><topic>Unusual amino acids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tanaka, Minoru</creatorcontrib><creatorcontrib>Hikawa, Hidemasa</creatorcontrib><creatorcontrib>Yokoyama, Yuusaku</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tanaka, Minoru</au><au>Hikawa, Hidemasa</au><au>Yokoyama, Yuusaku</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Convenient synthesis of chiral tryptophan derivatives using Negishi cross-coupling</atitle><jtitle>Tetrahedron</jtitle><date>2011-08-19</date><risdate>2011</risdate><volume>67</volume><issue>33</issue><spage>5897</spage><epage>5901</epage><pages>5897-5901</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>A facile synthetic procedure for chiral tryptophan derivatives using Negishi cross-coupling reaction of serine-derived iodoalanine with 3-haloindole is described. The best result was obtained when the reaction of
N-tosyl-3-bromoindole with
N-Cbz-iodoalanine methyl ester was carried out by the combination of Pd
2(dba)
3 and sterically hindered ferrocenyl ligand Q-PHOS. This reaction condition not only gave the desired tryptophan derivative as high as 76% yield, but also suppressed the formation of undesired products, the dehalogenated indole and the homodimer of indole, which were difficult to separate. This reaction was extended to the synthesis of various tryptophan derivatives having substituents on the benzene ring. The characteristic of this reaction is the practical biomimetic synthesis of chiral tryptophan derivatives in one-step.
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| subjects | Biomimetic synthesis Biomimetics Chemical reactions Chemistry Derivatives Esters Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indoles Ligands Negishi cross-coupling Noncondensed benzenic compounds Organic chemistry Preparations and properties Synthesis (chemistry) Tryptophan Unusual amino acids |
| title | Convenient synthesis of chiral tryptophan derivatives using Negishi cross-coupling |
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