Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-Proline-Catalysed α-Aminooxylation
An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)‐α‐conhydrine (98 % ee) and (–)‐sedamine (95 % ee), by L‐proline‐catalysed α‐aminooxylation of aldehydes has been developed. The strategy involves an intramolecular cyclization to...
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| Veröffentlicht in: | European Journal of Organic Chemistry 2010-06, Vol.2010 (18), p.3437-3444 |
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| container_title | European Journal of Organic Chemistry |
| container_volume | 2010 |
| creator | Shaikh, Tanveer Mahamadali Sudalai, Arumugam |
| description | An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)‐α‐conhydrine (98 % ee) and (–)‐sedamine (95 % ee), by L‐proline‐catalysed α‐aminooxylation of aldehydes has been developed. The strategy involves an intramolecular cyclization to construct the piperidine core.
The piperidine ring is a ubiquitous structural motif present in numerous naturally occurring alkaloids and can be frequently recognized in the structures of drug candidates. Conhydrine and sedamine are two such alkaloids, and their enantioselective synthesis has been achieved in good overall yields. |
| doi_str_mv | 10.1002/ejoc.201000169 |
| format | Article |
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The piperidine ring is a ubiquitous structural motif present in numerous naturally occurring alkaloids and can be frequently recognized in the structures of drug candidates. Conhydrine and sedamine are two such alkaloids, and their enantioselective synthesis has been achieved in good overall yields.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201000169</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkaloids ; Amino acids ; Aminooxylation ; Chemistry ; Enantioselectivity ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Organocatalysis ; Preparations and properties</subject><ispartof>European Journal of Organic Chemistry, 2010-06, Vol.2010 (18), p.3437-3444</ispartof><rights>Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2879-535fbb589ceb4a22fa65eae00503d65cef22ca5dc7ebb06b3ed1ecbfd95c5a33</citedby><cites>FETCH-LOGICAL-c2879-535fbb589ceb4a22fa65eae00503d65cef22ca5dc7ebb06b3ed1ecbfd95c5a33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201000169$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201000169$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>313,314,776,780,788,1411,27901,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22922885$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Shaikh, Tanveer Mahamadali</creatorcontrib><creatorcontrib>Sudalai, Arumugam</creatorcontrib><title>Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-Proline-Catalysed α-Aminooxylation</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)‐α‐conhydrine (98 % ee) and (–)‐sedamine (95 % ee), by L‐proline‐catalysed α‐aminooxylation of aldehydes has been developed. The strategy involves an intramolecular cyclization to construct the piperidine core.
The piperidine ring is a ubiquitous structural motif present in numerous naturally occurring alkaloids and can be frequently recognized in the structures of drug candidates. Conhydrine and sedamine are two such alkaloids, and their enantioselective synthesis has been achieved in good overall yields.</description><subject>Alkaloids</subject><subject>Amino acids</subject><subject>Aminooxylation</subject><subject>Chemistry</subject><subject>Enantioselectivity</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>Organic chemistry</subject><subject>Organocatalysis</subject><subject>Preparations and properties</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqFkM1Kw0AUhYMoWKtb19kIFZk6P51pZylprUpRUVF3w83khk6NSckEbR7LF_GZnFIp7lzdv_OdCyeKjhntM0r5OS4q2-c09JQpvRN1GNWaUKXpbugHYkCYFq_70YH3i6DRSrFO5CYllI2rPBZoG_eB8WNbNnP0zsdVHvfOTsn3F0mqct5mtSsxhjKLe-SUPGIG7-tF2sYzcl9XRRhIAg0UrccsDtRFuFfVqi0gPCgPo70cCo9Hv7UbPV1OnpIrMrubXicXM2L5aKiJFDJPUznSFtMBcJ6DkghIqaQiU9JizrkFmdkhpilVqcCMoU3zTEsrQYhu1N_Y2rryvsbcLGv3DnVrGDXrnMw6J7PNKQAnG2AJ3kKR11Ba57cU55rz0UgGnd7oPl2B7T-uZnJzl_z9QTas8w2utizUb0YNxVCal9upuXpQ4-fxYGqY-AG0Eoua</recordid><startdate>201006</startdate><enddate>201006</enddate><creator>Shaikh, Tanveer Mahamadali</creator><creator>Sudalai, Arumugam</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201006</creationdate><title>Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-Proline-Catalysed α-Aminooxylation</title><author>Shaikh, Tanveer Mahamadali ; Sudalai, Arumugam</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2879-535fbb589ceb4a22fa65eae00503d65cef22ca5dc7ebb06b3ed1ecbfd95c5a33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Alkaloids</topic><topic>Amino acids</topic><topic>Aminooxylation</topic><topic>Chemistry</topic><topic>Enantioselectivity</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>Organic chemistry</topic><topic>Organocatalysis</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shaikh, Tanveer Mahamadali</creatorcontrib><creatorcontrib>Sudalai, Arumugam</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shaikh, Tanveer Mahamadali</au><au>Sudalai, Arumugam</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-Proline-Catalysed α-Aminooxylation</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2010-06</date><risdate>2010</risdate><volume>2010</volume><issue>18</issue><spage>3437</spage><epage>3444</epage><pages>3437-3444</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)‐α‐conhydrine (98 % ee) and (–)‐sedamine (95 % ee), by L‐proline‐catalysed α‐aminooxylation of aldehydes has been developed. The strategy involves an intramolecular cyclization to construct the piperidine core.
The piperidine ring is a ubiquitous structural motif present in numerous naturally occurring alkaloids and can be frequently recognized in the structures of drug candidates. Conhydrine and sedamine are two such alkaloids, and their enantioselective synthesis has been achieved in good overall yields.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201000169</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1434-193X |
| ispartof | European Journal of Organic Chemistry, 2010-06, Vol.2010 (18), p.3437-3444 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ejoc_201000169 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkaloids Amino acids Aminooxylation Chemistry Enantioselectivity Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Organocatalysis Preparations and properties |
| title | Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-Proline-Catalysed α-Aminooxylation |
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