Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates
We developed an asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2-carboxylates using 10 mol% of a chiral phosphoric acid. The products, which are novel bisindole-piperidine-amino acid hybrids, can be obtained in one step from 3-vinyl indoles with imino esters in dichlorome...
Gespeichert in:
| Veröffentlicht in: | Organic & biomolecular chemistry 2014-05, Vol.12 (20), p.3265-3270 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3270 |
|---|---|
| container_issue | 20 |
| container_start_page | 3265 |
| container_title | Organic & biomolecular chemistry |
| container_volume | 12 |
| creator | Zhong, Sabilla Nieger, Martin Bihlmeier, Angela Shi, Min Bräse, Stefan |
| description | We developed an asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2-carboxylates using 10 mol% of a chiral phosphoric acid. The products, which are novel bisindole-piperidine-amino acid hybrids, can be obtained in one step from 3-vinyl indoles with imino esters in dichloromethane at room temperature after 1 h of reaction time. A variety of these compounds could be synthesized in up to 70% yield and 99% ee, and they were experimentally and computationally analyzed regarding their relative and absolute stereochemistry. |
| doi_str_mv | 10.1039/c4ob00234b |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1518814584</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1518814584</sourcerecordid><originalsourceid>FETCH-LOGICAL-c323t-c5b0c2429746292228644d47942ee3cfdcf3bc06e5252747e04b9a68abcb484d3</originalsourceid><addsrcrecordid>eNo9kMtOwzAURC0EoqWw4QNQlgVh8OPmtWwroEiVuoEFq8h2bsAoiYOdSuTvKbR0NTPS0SwOIZec3XEm83sDTjMmJOgjMuaQppTFMj8-dMFG5CyET8Z4niZwSkYCUik5wJi8zcLQNNh7ayLn31XrjOpVPfTbHYa2_8BgQ-SqCG4Tqm2Y8iW1belqpJIO9TXtbIfelrZFKiKjvHbfQ616DOfkpFJ1wIt9Tsjr48PLYklX66fnxWxFjRSypybWzAgQeQqJyIUQWQJQQpqDQJSmKk0ltWEJxiIWKaTIQOcqyZQ2GjIo5YRMd7-dd18bDH3R2GCwrlWLbhMKHvMs4xBnsEVvdqjxLgSPVdF52yg_FJwVvyqLBaznfyrnW_hq_7vRDZYH9N-d_AFWV22L</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1518814584</pqid></control><display><type>article</type><title>Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals</source><source>Alma/SFX Local Collection</source><creator>Zhong, Sabilla ; Nieger, Martin ; Bihlmeier, Angela ; Shi, Min ; Bräse, Stefan</creator><creatorcontrib>Zhong, Sabilla ; Nieger, Martin ; Bihlmeier, Angela ; Shi, Min ; Bräse, Stefan</creatorcontrib><description>We developed an asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2-carboxylates using 10 mol% of a chiral phosphoric acid. The products, which are novel bisindole-piperidine-amino acid hybrids, can be obtained in one step from 3-vinyl indoles with imino esters in dichloromethane at room temperature after 1 h of reaction time. A variety of these compounds could be synthesized in up to 70% yield and 99% ee, and they were experimentally and computationally analyzed regarding their relative and absolute stereochemistry.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c4ob00234b</identifier><identifier>PMID: 24733144</identifier><language>eng</language><publisher>England</publisher><subject>Amino Acids - chemistry ; Catalysis ; Chemistry, Organic - methods ; Circular Dichroism ; Imines - chemistry ; Indole Alkaloids - chemical synthesis ; Indole Alkaloids - chemistry ; Phosphoric Acids - chemistry ; Piperidines - chemical synthesis ; Piperidines - chemistry ; Thiourea - chemistry</subject><ispartof>Organic & biomolecular chemistry, 2014-05, Vol.12 (20), p.3265-3270</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c323t-c5b0c2429746292228644d47942ee3cfdcf3bc06e5252747e04b9a68abcb484d3</citedby><cites>FETCH-LOGICAL-c323t-c5b0c2429746292228644d47942ee3cfdcf3bc06e5252747e04b9a68abcb484d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24733144$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhong, Sabilla</creatorcontrib><creatorcontrib>Nieger, Martin</creatorcontrib><creatorcontrib>Bihlmeier, Angela</creatorcontrib><creatorcontrib>Shi, Min</creatorcontrib><creatorcontrib>Bräse, Stefan</creatorcontrib><title>Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>We developed an asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2-carboxylates using 10 mol% of a chiral phosphoric acid. The products, which are novel bisindole-piperidine-amino acid hybrids, can be obtained in one step from 3-vinyl indoles with imino esters in dichloromethane at room temperature after 1 h of reaction time. A variety of these compounds could be synthesized in up to 70% yield and 99% ee, and they were experimentally and computationally analyzed regarding their relative and absolute stereochemistry.</description><subject>Amino Acids - chemistry</subject><subject>Catalysis</subject><subject>Chemistry, Organic - methods</subject><subject>Circular Dichroism</subject><subject>Imines - chemistry</subject><subject>Indole Alkaloids - chemical synthesis</subject><subject>Indole Alkaloids - chemistry</subject><subject>Phosphoric Acids - chemistry</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - chemistry</subject><subject>Thiourea - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kMtOwzAURC0EoqWw4QNQlgVh8OPmtWwroEiVuoEFq8h2bsAoiYOdSuTvKbR0NTPS0SwOIZec3XEm83sDTjMmJOgjMuaQppTFMj8-dMFG5CyET8Z4niZwSkYCUik5wJi8zcLQNNh7ayLn31XrjOpVPfTbHYa2_8BgQ-SqCG4Tqm2Y8iW1belqpJIO9TXtbIfelrZFKiKjvHbfQ616DOfkpFJ1wIt9Tsjr48PLYklX66fnxWxFjRSypybWzAgQeQqJyIUQWQJQQpqDQJSmKk0ltWEJxiIWKaTIQOcqyZQ2GjIo5YRMd7-dd18bDH3R2GCwrlWLbhMKHvMs4xBnsEVvdqjxLgSPVdF52yg_FJwVvyqLBaznfyrnW_hq_7vRDZYH9N-d_AFWV22L</recordid><startdate>20140528</startdate><enddate>20140528</enddate><creator>Zhong, Sabilla</creator><creator>Nieger, Martin</creator><creator>Bihlmeier, Angela</creator><creator>Shi, Min</creator><creator>Bräse, Stefan</creator><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>20140528</creationdate><title>Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates</title><author>Zhong, Sabilla ; Nieger, Martin ; Bihlmeier, Angela ; Shi, Min ; Bräse, Stefan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c323t-c5b0c2429746292228644d47942ee3cfdcf3bc06e5252747e04b9a68abcb484d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Amino Acids - chemistry</topic><topic>Catalysis</topic><topic>Chemistry, Organic - methods</topic><topic>Circular Dichroism</topic><topic>Imines - chemistry</topic><topic>Indole Alkaloids - chemical synthesis</topic><topic>Indole Alkaloids - chemistry</topic><topic>Phosphoric Acids - chemistry</topic><topic>Piperidines - chemical synthesis</topic><topic>Piperidines - chemistry</topic><topic>Thiourea - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhong, Sabilla</creatorcontrib><creatorcontrib>Nieger, Martin</creatorcontrib><creatorcontrib>Bihlmeier, Angela</creatorcontrib><creatorcontrib>Shi, Min</creatorcontrib><creatorcontrib>Bräse, Stefan</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 & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhong, Sabilla</au><au>Nieger, Martin</au><au>Bihlmeier, Angela</au><au>Shi, Min</au><au>Bräse, Stefan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2014-05-28</date><risdate>2014</risdate><volume>12</volume><issue>20</issue><spage>3265</spage><epage>3270</epage><pages>3265-3270</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>We developed an asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2-carboxylates using 10 mol% of a chiral phosphoric acid. The products, which are novel bisindole-piperidine-amino acid hybrids, can be obtained in one step from 3-vinyl indoles with imino esters in dichloromethane at room temperature after 1 h of reaction time. A variety of these compounds could be synthesized in up to 70% yield and 99% ee, and they were experimentally and computationally analyzed regarding their relative and absolute stereochemistry.</abstract><cop>England</cop><pmid>24733144</pmid><doi>10.1039/c4ob00234b</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2014-05, Vol.12 (20), p.3265-3270 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1518814584 |
| source | MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Amino Acids - chemistry Catalysis Chemistry, Organic - methods Circular Dichroism Imines - chemistry Indole Alkaloids - chemical synthesis Indole Alkaloids - chemistry Phosphoric Acids - chemistry Piperidines - chemical synthesis Piperidines - chemistry Thiourea - chemistry |
| title | Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-18T20%3A23%3A49IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Asymmetric%20organocatalytic%20synthesis%20of%204,6-bis(1H-indole-3-yl)-piperidine-2%20carboxylates&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Zhong,%20Sabilla&rft.date=2014-05-28&rft.volume=12&rft.issue=20&rft.spage=3265&rft.epage=3270&rft.pages=3265-3270&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/c4ob00234b&rft_dat=%3Cproquest_cross%3E1518814584%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1518814584&rft_id=info:pmid/24733144&rfr_iscdi=true |