Base‐Promoted Cycloaddition of γ‐Hydroxy‐ and δ‐Hydroxy‐α,β‐Unsaturated Carbonyls with Azaoxyallyl Cations: Rapid Synthesis of N,O‐Heterocycles
Metal‐free and environmentally friendly synthesis of morpholin‐3‐one and 1,4‐oxazepan‐3‐one skeletons was achieved by the cycloaddition reaction of alcohol‐tethered enones and α‐halohydroxamates. This transformation was proposed to proceed through the addition of the hydroxyl group in the enone to a...
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| Veröffentlicht in: | European journal of organic chemistry 2020-05, Vol.2020 (20), p.3090-3100 |
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| container_title | European journal of organic chemistry |
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| creator | Son, Eun Chae Lee, Jiseon Kim, Sung‐Gon |
| description | Metal‐free and environmentally friendly synthesis of morpholin‐3‐one and 1,4‐oxazepan‐3‐one skeletons was achieved by the cycloaddition reaction of alcohol‐tethered enones and α‐halohydroxamates. This transformation was proposed to proceed through the addition of the hydroxyl group in the enone to an in‐situ generated azaoxyallyl cation followed by intramolecular aza‐Michael‐type trapping. Accordingly, morpholin‐3‐ones and 1,4‐oxazepan‐3‐ones could be generated from γ‐hydroxy and δ‐hydroxy enones, respectively, in a highly diastereoselective manner.
The synthesis of morpholin‐3‐one and 1,4‐oxazepan‐3‐one skeletons was achieved by the cycloaddition reaction of alcohol‐tethered enones and α‐halohydroxamates. This process proceeds through the addition of the hydroxyl group in the enone to an in‐situ generated azaoxyallyl cation followed by intramolecular aza‐Michael‐type trapping. Morpholin‐3‐ones and 1,4‐oxazepan‐3‐ones could be generated from γ‐hydroxy and δ‐hydroxy enones, respectively. |
| doi_str_mv | 10.1002/ejoc.202000368 |
| format | Article |
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The synthesis of morpholin‐3‐one and 1,4‐oxazepan‐3‐one skeletons was achieved by the cycloaddition reaction of alcohol‐tethered enones and α‐halohydroxamates. This process proceeds through the addition of the hydroxyl group in the enone to an in‐situ generated azaoxyallyl cation followed by intramolecular aza‐Michael‐type trapping. Morpholin‐3‐ones and 1,4‐oxazepan‐3‐ones could be generated from γ‐hydroxy and δ‐hydroxy enones, respectively.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202000368</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Azaoxyallyl cation ; Carbonyls ; Cations ; Cycloaddition ; Hydroxyl groups ; Morpholinone ; N,O‐Heterocycles ; Oxazepanone ; Stereoselectivity ; Synthesis</subject><ispartof>European journal of organic chemistry, 2020-05, Vol.2020 (20), p.3090-3100</ispartof><rights>2020 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3178-3805bc268730c49b4b3505eb342d10fe2304caa4124f52c99fbbfdd97f635be93</citedby><cites>FETCH-LOGICAL-c3178-3805bc268730c49b4b3505eb342d10fe2304caa4124f52c99fbbfdd97f635be93</cites><orcidid>0000-0001-5099-0944</orcidid></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.202000368$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202000368$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Son, Eun Chae</creatorcontrib><creatorcontrib>Lee, Jiseon</creatorcontrib><creatorcontrib>Kim, Sung‐Gon</creatorcontrib><title>Base‐Promoted Cycloaddition of γ‐Hydroxy‐ and δ‐Hydroxy‐α,β‐Unsaturated Carbonyls with Azaoxyallyl Cations: Rapid Synthesis of N,O‐Heterocycles</title><title>European journal of organic chemistry</title><description>Metal‐free and environmentally friendly synthesis of morpholin‐3‐one and 1,4‐oxazepan‐3‐one skeletons was achieved by the cycloaddition reaction of alcohol‐tethered enones and α‐halohydroxamates. This transformation was proposed to proceed through the addition of the hydroxyl group in the enone to an in‐situ generated azaoxyallyl cation followed by intramolecular aza‐Michael‐type trapping. Accordingly, morpholin‐3‐ones and 1,4‐oxazepan‐3‐ones could be generated from γ‐hydroxy and δ‐hydroxy enones, respectively, in a highly diastereoselective manner.
The synthesis of morpholin‐3‐one and 1,4‐oxazepan‐3‐one skeletons was achieved by the cycloaddition reaction of alcohol‐tethered enones and α‐halohydroxamates. This process proceeds through the addition of the hydroxyl group in the enone to an in‐situ generated azaoxyallyl cation followed by intramolecular aza‐Michael‐type trapping. Morpholin‐3‐ones and 1,4‐oxazepan‐3‐ones could be generated from γ‐hydroxy and δ‐hydroxy enones, respectively.</description><subject>Azaoxyallyl cation</subject><subject>Carbonyls</subject><subject>Cations</subject><subject>Cycloaddition</subject><subject>Hydroxyl groups</subject><subject>Morpholinone</subject><subject>N,O‐Heterocycles</subject><subject>Oxazepanone</subject><subject>Stereoselectivity</subject><subject>Synthesis</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkUtOwzAQhiMEEs8ta0tsSRk_ktTsoCovIYqASuwix3bUVCEudioIK47AFTgCj3P0EJwEhyIQK1Yzmvn-f0b6g2ATQwcDkB09NrJDgAAAjbsLwQoGzkOIOSz6nlEWYk6vl4NV58ae4XGMV4LnfeH0x-PTuTU3ptYK9RpZGqFUURemQiZHsze_PmqUNfeN75CoFJq9_5nNXrZnr74OKyfqqRVfPsJmpmpKh-6KeoT2HoRnRVk2pV-13m4XXYhJodBlU9Uj7QrXXjvbHrTWutbWSP-KduvBUi5Kpze-61owPOhf9Y7C08HhcW_vNJQUJ92QdiHKJIm7CQXJeMYyGkGkM8qIwpBrQoFJIRgmLI-I5DzPslwpnuQxjTLN6VqwNfedWHM71a5Ox2ZqK38yJQySCCcMR57qzClpjXNW5-nEFjfCNimGtI0hbWNIf2LwAj4X3BWlbv6h0_7JoPer_QRhSZiN</recordid><startdate>20200529</startdate><enddate>20200529</enddate><creator>Son, Eun Chae</creator><creator>Lee, Jiseon</creator><creator>Kim, Sung‐Gon</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-5099-0944</orcidid></search><sort><creationdate>20200529</creationdate><title>Base‐Promoted Cycloaddition of γ‐Hydroxy‐ and δ‐Hydroxy‐α,β‐Unsaturated Carbonyls with Azaoxyallyl Cations: Rapid Synthesis of N,O‐Heterocycles</title><author>Son, Eun Chae ; Lee, Jiseon ; Kim, Sung‐Gon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3178-3805bc268730c49b4b3505eb342d10fe2304caa4124f52c99fbbfdd97f635be93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Azaoxyallyl cation</topic><topic>Carbonyls</topic><topic>Cations</topic><topic>Cycloaddition</topic><topic>Hydroxyl groups</topic><topic>Morpholinone</topic><topic>N,O‐Heterocycles</topic><topic>Oxazepanone</topic><topic>Stereoselectivity</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Son, Eun Chae</creatorcontrib><creatorcontrib>Lee, Jiseon</creatorcontrib><creatorcontrib>Kim, Sung‐Gon</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Son, Eun Chae</au><au>Lee, Jiseon</au><au>Kim, Sung‐Gon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Base‐Promoted Cycloaddition of γ‐Hydroxy‐ and δ‐Hydroxy‐α,β‐Unsaturated Carbonyls with Azaoxyallyl Cations: Rapid Synthesis of N,O‐Heterocycles</atitle><jtitle>European journal of organic chemistry</jtitle><date>2020-05-29</date><risdate>2020</risdate><volume>2020</volume><issue>20</issue><spage>3090</spage><epage>3100</epage><pages>3090-3100</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Metal‐free and environmentally friendly synthesis of morpholin‐3‐one and 1,4‐oxazepan‐3‐one skeletons was achieved by the cycloaddition reaction of alcohol‐tethered enones and α‐halohydroxamates. This transformation was proposed to proceed through the addition of the hydroxyl group in the enone to an in‐situ generated azaoxyallyl cation followed by intramolecular aza‐Michael‐type trapping. Accordingly, morpholin‐3‐ones and 1,4‐oxazepan‐3‐ones could be generated from γ‐hydroxy and δ‐hydroxy enones, respectively, in a highly diastereoselective manner.
The synthesis of morpholin‐3‐one and 1,4‐oxazepan‐3‐one skeletons was achieved by the cycloaddition reaction of alcohol‐tethered enones and α‐halohydroxamates. This process proceeds through the addition of the hydroxyl group in the enone to an in‐situ generated azaoxyallyl cation followed by intramolecular aza‐Michael‐type trapping. Morpholin‐3‐ones and 1,4‐oxazepan‐3‐ones could be generated from γ‐hydroxy and δ‐hydroxy enones, respectively.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202000368</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0001-5099-0944</orcidid></addata></record> |
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| subjects | Azaoxyallyl cation Carbonyls Cations Cycloaddition Hydroxyl groups Morpholinone N,O‐Heterocycles Oxazepanone Stereoselectivity Synthesis |
| title | Base‐Promoted Cycloaddition of γ‐Hydroxy‐ and δ‐Hydroxy‐α,β‐Unsaturated Carbonyls with Azaoxyallyl Cations: Rapid Synthesis of N,O‐Heterocycles |
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