Synthesis of 1,3-Diaminated Stereotriads via Rearrangement of 1,4-Diazaspiro[2.2]pentanes
The synthesis of 1,3-diaminated stereotriads via the bis-aziridination of allenes is reported. The reactive 1,4-diazaspiro[2.2]pentane intermediates undergo a mild Brønsted acid-promoted rearrangement to yield 1,3-diaminated ketones in good yields with excellent stereocontrol. Directed reduction of...
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| Veröffentlicht in: | Organic letters 2012-04, Vol.14 (7), p.1704-1707 |
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| creator | Weatherly, Cale D Rigoli, Jared W Schomaker, Jennifer M |
| description | The synthesis of 1,3-diaminated stereotriads via the bis-aziridination of allenes is reported. The reactive 1,4-diazaspiro[2.2]pentane intermediates undergo a mild Brønsted acid-promoted rearrangement to yield 1,3-diaminated ketones in good yields with excellent stereocontrol. Directed reduction of the ketone can be achieved to yield a C–N/C–O/C–N stereotriad in high dr. The ability to transfer the axial chirality of the substrates to the products allows for the facile preparation of enantioenriched stereotriads from allenes in two simple steps. |
| doi_str_mv | 10.1021/ol300269u |
| format | Article |
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The reactive 1,4-diazaspiro[2.2]pentane intermediates undergo a mild Brønsted acid-promoted rearrangement to yield 1,3-diaminated ketones in good yields with excellent stereocontrol. Directed reduction of the ketone can be achieved to yield a C–N/C–O/C–N stereotriad in high dr. The ability to transfer the axial chirality of the substrates to the products allows for the facile preparation of enantioenriched stereotriads from allenes in two simple steps.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol300269u</identifier><identifier>PMID: 22433023</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkadienes - chemistry ; Aza Compounds - chemical synthesis ; Aza Compounds - chemistry ; Catalysis ; Imidazolidines - chemical synthesis ; Imidazolidines - chemistry ; Ketones - chemical synthesis ; Ketones - chemistry ; Molecular Structure ; Pyrimidines - chemical synthesis ; Pyrimidines - chemistry ; Pyrroles - chemical synthesis ; Pyrroles - chemistry ; Spiro Compounds - chemistry</subject><ispartof>Organic letters, 2012-04, Vol.14 (7), p.1704-1707</ispartof><rights>Copyright © 2012 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a404t-ab5b9f51e38858350dd7a1df0e4e7802bacbc41bd5774fccfdcec83ca4bfb8923</citedby><cites>FETCH-LOGICAL-a404t-ab5b9f51e38858350dd7a1df0e4e7802bacbc41bd5774fccfdcec83ca4bfb8923</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol300269u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol300269u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22433023$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Weatherly, Cale D</creatorcontrib><creatorcontrib>Rigoli, Jared W</creatorcontrib><creatorcontrib>Schomaker, Jennifer M</creatorcontrib><title>Synthesis of 1,3-Diaminated Stereotriads via Rearrangement of 1,4-Diazaspiro[2.2]pentanes</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The synthesis of 1,3-diaminated stereotriads via the bis-aziridination of allenes is reported. The reactive 1,4-diazaspiro[2.2]pentane intermediates undergo a mild Brønsted acid-promoted rearrangement to yield 1,3-diaminated ketones in good yields with excellent stereocontrol. Directed reduction of the ketone can be achieved to yield a C–N/C–O/C–N stereotriad in high dr. The ability to transfer the axial chirality of the substrates to the products allows for the facile preparation of enantioenriched stereotriads from allenes in two simple steps.</description><subject>Alkadienes - chemistry</subject><subject>Aza Compounds - chemical synthesis</subject><subject>Aza Compounds - chemistry</subject><subject>Catalysis</subject><subject>Imidazolidines - chemical synthesis</subject><subject>Imidazolidines - chemistry</subject><subject>Ketones - chemical synthesis</subject><subject>Ketones - chemistry</subject><subject>Molecular Structure</subject><subject>Pyrimidines - chemical synthesis</subject><subject>Pyrimidines - chemistry</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - chemistry</subject><subject>Spiro Compounds - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkVtLxDAQhYMoXlYf_APSFxHBam7dti-CrFcQBC8PIhKm6dSNtM2atAvrrzfL6qLgU0LON2cmZwjZZfSYUc5ObC0o5cO8XyGbLOEiTmnCV5f3Id0gW96_U8rCS75ONjiXQlAuNsnzw6ztxuiNj2wVsSMRnxtoTAsdltFDhw5t5wyUPpoaiO4RnIP2DRtsu0WBnBd8gp8YZ1_4MX-dBAla9NtkrYLa4873OSBPlxePo-v49u7qZnR2G4OksouhSIq8ShiKLEsykdCyTIGVFUWJaUZ5AbrQkhVlkqay0roqNepMaJBFVWQ5FwNyuvCd9EWDQW07B7WaONOAmykLRv1VWjNWb3aqpMxpJmgwOPg2cPajR9-pxniNdR1-YXuv8pwHTDIWyMMFqZ313mG17MKomm9CLTcR2L3fYy3Jn-gDsL8AQHv1bnvXhpT-MfoC9SiRlw</recordid><startdate>20120406</startdate><enddate>20120406</enddate><creator>Weatherly, Cale D</creator><creator>Rigoli, Jared W</creator><creator>Schomaker, Jennifer M</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><scope>5PM</scope></search><sort><creationdate>20120406</creationdate><title>Synthesis of 1,3-Diaminated Stereotriads via Rearrangement of 1,4-Diazaspiro[2.2]pentanes</title><author>Weatherly, Cale D ; Rigoli, Jared W ; Schomaker, Jennifer M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a404t-ab5b9f51e38858350dd7a1df0e4e7802bacbc41bd5774fccfdcec83ca4bfb8923</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alkadienes - chemistry</topic><topic>Aza Compounds - chemical synthesis</topic><topic>Aza Compounds - chemistry</topic><topic>Catalysis</topic><topic>Imidazolidines - chemical synthesis</topic><topic>Imidazolidines - chemistry</topic><topic>Ketones - chemical synthesis</topic><topic>Ketones - chemistry</topic><topic>Molecular Structure</topic><topic>Pyrimidines - chemical synthesis</topic><topic>Pyrimidines - chemistry</topic><topic>Pyrroles - chemical synthesis</topic><topic>Pyrroles - chemistry</topic><topic>Spiro Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Weatherly, Cale D</creatorcontrib><creatorcontrib>Rigoli, Jared W</creatorcontrib><creatorcontrib>Schomaker, Jennifer M</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><collection>PubMed Central (Full Participant titles)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Weatherly, Cale D</au><au>Rigoli, Jared W</au><au>Schomaker, Jennifer M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 1,3-Diaminated Stereotriads via Rearrangement of 1,4-Diazaspiro[2.2]pentanes</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2012-04-06</date><risdate>2012</risdate><volume>14</volume><issue>7</issue><spage>1704</spage><epage>1707</epage><pages>1704-1707</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The synthesis of 1,3-diaminated stereotriads via the bis-aziridination of allenes is reported. The reactive 1,4-diazaspiro[2.2]pentane intermediates undergo a mild Brønsted acid-promoted rearrangement to yield 1,3-diaminated ketones in good yields with excellent stereocontrol. Directed reduction of the ketone can be achieved to yield a C–N/C–O/C–N stereotriad in high dr. The ability to transfer the axial chirality of the substrates to the products allows for the facile preparation of enantioenriched stereotriads from allenes in two simple steps.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>22433023</pmid><doi>10.1021/ol300269u</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2012-04, Vol.14 (7), p.1704-1707 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Alkadienes - chemistry Aza Compounds - chemical synthesis Aza Compounds - chemistry Catalysis Imidazolidines - chemical synthesis Imidazolidines - chemistry Ketones - chemical synthesis Ketones - chemistry Molecular Structure Pyrimidines - chemical synthesis Pyrimidines - chemistry Pyrroles - chemical synthesis Pyrroles - chemistry Spiro Compounds - chemistry |
| title | Synthesis of 1,3-Diaminated Stereotriads via Rearrangement of 1,4-Diazaspiro[2.2]pentanes |
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