Direct Synthesis of Chiral 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via a Catalytic Asymmetric Intramolecular Aza-Friedel–Crafts Reaction
The direct asymmetric intramolecular aza-Friedel–Crafts reaction of N-aminoethylpyrroles with aldehydes catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines with high yields and hig...
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| Veröffentlicht in: | Organic letters 2011-09, Vol.13 (17), p.4490-4493 |
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| container_end_page | 4493 |
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| container_issue | 17 |
| container_start_page | 4490 |
| container_title | Organic letters |
| container_volume | 13 |
| creator | He, Yuwei Lin, Maohui Li, Zhongmin Liang, Xinting Li, Guilong Antilla, Jon C |
| description | The direct asymmetric intramolecular aza-Friedel–Crafts reaction of N-aminoethylpyrroles with aldehydes catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines with high yields and high enantioselectivities. This strategy has been shown to be quite general toward various aldehydes and pyrrole derivatives. |
| doi_str_mv | 10.1021/ol2018328 |
| format | Article |
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This strategy has been shown to be quite general toward various aldehydes and pyrrole derivatives.</description><subject>Catalysis</subject><subject>Crystallography, X-Ray</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Phosphoric Acids - chemistry</subject><subject>Pyrazines - chemical synthesis</subject><subject>Pyrazines - chemistry</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM9q3DAQxkVJaP60h75A0aWEwLqVZMtrHRcnaQKBQP6cQjGz8phVkK2tJAecUx4gt75hn6Qqm-wpp_lm5jcfzEfIF86-cyb4D2cF41Uuqg9kn0uRZ3Mmxc5Wl2yPHITwwBhPE_WR7IlEF7JU--TlxHjUkd5MQ1xhMIG6jtYr48FSPhOzfFZktxg9rKbWu_XkvbPuPm0y-JU6eDIDBvpogAKtIYKdotF0Eaa-T1dJXgzpuHcW9WjB08UTZGfeYIv27_Of2kMXA71G0NG44RPZ7cAG_PxaD8nd2eltfZ5dXv28qBeXGeQVi9lcLQvBVNcxIRS2VcGVziXoudSKLVEC11qpvJS8KHnR5u2ya2UrBSsBeSG6_JAcbXzX3v0eMcSmN0GjtTCgG0NTVVKWQgmZyOMNqb0LwWPXrL3pwU8NZ83_7Jtt9on9-uo6Lntst-Rb2An4tgFAh-bBjX5IT75j9A-N3IwO</recordid><startdate>20110902</startdate><enddate>20110902</enddate><creator>He, Yuwei</creator><creator>Lin, Maohui</creator><creator>Li, Zhongmin</creator><creator>Liang, Xinting</creator><creator>Li, Guilong</creator><creator>Antilla, Jon C</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20110902</creationdate><title>Direct Synthesis of Chiral 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via a Catalytic Asymmetric Intramolecular Aza-Friedel–Crafts Reaction</title><author>He, Yuwei ; Lin, Maohui ; Li, Zhongmin ; Liang, Xinting ; Li, Guilong ; Antilla, Jon C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a380t-79b4209ff0229ed8419c35ac75c90be5a1cc9936514614d3dbfd5d5206ae142f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Catalysis</topic><topic>Crystallography, X-Ray</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Phosphoric Acids - chemistry</topic><topic>Pyrazines - chemical synthesis</topic><topic>Pyrazines - chemistry</topic><topic>Pyrroles - chemical synthesis</topic><topic>Pyrroles - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>He, Yuwei</creatorcontrib><creatorcontrib>Lin, Maohui</creatorcontrib><creatorcontrib>Li, Zhongmin</creatorcontrib><creatorcontrib>Liang, Xinting</creatorcontrib><creatorcontrib>Li, Guilong</creatorcontrib><creatorcontrib>Antilla, Jon C</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>He, Yuwei</au><au>Lin, Maohui</au><au>Li, Zhongmin</au><au>Liang, Xinting</au><au>Li, Guilong</au><au>Antilla, Jon C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct Synthesis of Chiral 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via a Catalytic Asymmetric Intramolecular Aza-Friedel–Crafts Reaction</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| ispartof | Organic letters, 2011-09, Vol.13 (17), p.4490-4493 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Catalysis Crystallography, X-Ray Models, Molecular Molecular Structure Phosphoric Acids - chemistry Pyrazines - chemical synthesis Pyrazines - chemistry Pyrroles - chemical synthesis Pyrroles - chemistry Stereoisomerism |
| title | Direct Synthesis of Chiral 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via a Catalytic Asymmetric Intramolecular Aza-Friedel–Crafts Reaction |
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