Lithium Hydroxide Assisted Endo‐Selective [4+4]‐Photocycloaddition of Pyran‐2‐ones
3‐Acyl‐4‐hydroxypyan‐2‐ones with pendent furans, readily available from dehydroacetic acid, are substrates for intramolecular [4+4]‐photocycloaddition. In the presence of stoichiometric lithium base, these substrates undergo conversion to lactone‐bridged cyclooctenones in moderate to good yields upo...
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| Veröffentlicht in: | European journal of organic chemistry 2021-04, Vol.2021 (16), p.2294-2300 |
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| container_title | European journal of organic chemistry |
| container_volume | 2021 |
| creator | Li, Lei Turnbull, William L. McDonald, Robert West, F. G. |
| description | 3‐Acyl‐4‐hydroxypyan‐2‐ones with pendent furans, readily available from dehydroacetic acid, are substrates for intramolecular [4+4]‐photocycloaddition. In the presence of stoichiometric lithium base, these substrates undergo conversion to lactone‐bridged cyclooctenones in moderate to good yields upon irradiation in THF at 0 °C. In contrast to other crossed [4+4]‐photocycloadditions of pyran‐2‐ones, these examples proceed with complete diastereoselectivity for the endo cycloadducts.
Readily accessible 3‐acyl‐4‐hydroxypyran‐2‐ones with pendent furans undergo [4+4]‐photocycloaddition reactions in the presence of lithium ion to afford lactone‐bridged cyclooctenones with complete selectivity for the endo cycloadducts. |
| doi_str_mv | 10.1002/ejoc.202100122 |
| format | Article |
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Readily accessible 3‐acyl‐4‐hydroxypyran‐2‐ones with pendent furans undergo [4+4]‐photocycloaddition reactions in the presence of lithium ion to afford lactone‐bridged cyclooctenones with complete selectivity for the endo cycloadducts.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202100122</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkali metals ; Chelates ; Cycloaddition ; Furans ; Heterocycles ; Lithium ; Lithium hydroxides ; Photochemistry ; Stereoselectivity ; Substrates</subject><ispartof>European journal of organic chemistry, 2021-04, Vol.2021 (16), p.2294-2300</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3172-7030059db1f83f76d2c1294e470f852e1320a03967ec898b1bd0b1b6d6bc4ae83</citedby><cites>FETCH-LOGICAL-c3172-7030059db1f83f76d2c1294e470f852e1320a03967ec898b1bd0b1b6d6bc4ae83</cites><orcidid>0000-0001-7419-2314</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.202100122$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202100122$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Li, Lei</creatorcontrib><creatorcontrib>Turnbull, William L.</creatorcontrib><creatorcontrib>McDonald, Robert</creatorcontrib><creatorcontrib>West, F. G.</creatorcontrib><title>Lithium Hydroxide Assisted Endo‐Selective [4+4]‐Photocycloaddition of Pyran‐2‐ones</title><title>European journal of organic chemistry</title><description>3‐Acyl‐4‐hydroxypyan‐2‐ones with pendent furans, readily available from dehydroacetic acid, are substrates for intramolecular [4+4]‐photocycloaddition. In the presence of stoichiometric lithium base, these substrates undergo conversion to lactone‐bridged cyclooctenones in moderate to good yields upon irradiation in THF at 0 °C. In contrast to other crossed [4+4]‐photocycloadditions of pyran‐2‐ones, these examples proceed with complete diastereoselectivity for the endo cycloadducts.
Readily accessible 3‐acyl‐4‐hydroxypyran‐2‐ones with pendent furans undergo [4+4]‐photocycloaddition reactions in the presence of lithium ion to afford lactone‐bridged cyclooctenones with complete selectivity for the endo cycloadducts.</description><subject>Alkali metals</subject><subject>Chelates</subject><subject>Cycloaddition</subject><subject>Furans</subject><subject>Heterocycles</subject><subject>Lithium</subject><subject>Lithium hydroxides</subject><subject>Photochemistry</subject><subject>Stereoselectivity</subject><subject>Substrates</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFUE1Lw0AQXUTBWr16DniUxNmPJtljKdUqhRZUEEWWZHdDt6TZupuqufkT_I3-ErdU9OhhZt7MvDcDD6FTDAkGIBd6aWVCgIQGE7KHehg4jyHlsB8woyzGnD4coiPvlwDA0xT30OPUtAuzWUWTTjn7bpSOht4b32oVjRtlvz4-b3WtZWtedfTEztlzmMwXtrWyk7UtlDKtsU1kq2jeuaIJWxLCNtofo4OqqL0--al9dH85vhtN4uns6no0nMaS4ozEGVCAAVclrnJaZakiEhPONMugygdEY0qgAMrTTMuc5yUuFYSUqrSUrNA57aOz3d21sy8b7VuxtBvXhJeCDHDOKWMkC6xkx5LOeu90JdbOrArXCQxi65_Y-id-_QsCvhO8mVp3_7DF-GY2-tN-AzNjd3A</recordid><startdate>20210426</startdate><enddate>20210426</enddate><creator>Li, Lei</creator><creator>Turnbull, William L.</creator><creator>McDonald, Robert</creator><creator>West, F. G.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-7419-2314</orcidid></search><sort><creationdate>20210426</creationdate><title>Lithium Hydroxide Assisted Endo‐Selective [4+4]‐Photocycloaddition of Pyran‐2‐ones</title><author>Li, Lei ; Turnbull, William L. ; McDonald, Robert ; West, F. G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3172-7030059db1f83f76d2c1294e470f852e1320a03967ec898b1bd0b1b6d6bc4ae83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alkali metals</topic><topic>Chelates</topic><topic>Cycloaddition</topic><topic>Furans</topic><topic>Heterocycles</topic><topic>Lithium</topic><topic>Lithium hydroxides</topic><topic>Photochemistry</topic><topic>Stereoselectivity</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Lei</creatorcontrib><creatorcontrib>Turnbull, William L.</creatorcontrib><creatorcontrib>McDonald, Robert</creatorcontrib><creatorcontrib>West, F. G.</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Lei</au><au>Turnbull, William L.</au><au>McDonald, Robert</au><au>West, F. G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lithium Hydroxide Assisted Endo‐Selective [4+4]‐Photocycloaddition of Pyran‐2‐ones</atitle><jtitle>European journal of organic chemistry</jtitle><date>2021-04-26</date><risdate>2021</risdate><volume>2021</volume><issue>16</issue><spage>2294</spage><epage>2300</epage><pages>2294-2300</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>3‐Acyl‐4‐hydroxypyan‐2‐ones with pendent furans, readily available from dehydroacetic acid, are substrates for intramolecular [4+4]‐photocycloaddition. In the presence of stoichiometric lithium base, these substrates undergo conversion to lactone‐bridged cyclooctenones in moderate to good yields upon irradiation in THF at 0 °C. In contrast to other crossed [4+4]‐photocycloadditions of pyran‐2‐ones, these examples proceed with complete diastereoselectivity for the endo cycloadducts.
Readily accessible 3‐acyl‐4‐hydroxypyran‐2‐ones with pendent furans undergo [4+4]‐photocycloaddition reactions in the presence of lithium ion to afford lactone‐bridged cyclooctenones with complete selectivity for the endo cycloadducts.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202100122</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-7419-2314</orcidid></addata></record> |
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| ispartof | European journal of organic chemistry, 2021-04, Vol.2021 (16), p.2294-2300 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkali metals Chelates Cycloaddition Furans Heterocycles Lithium Lithium hydroxides Photochemistry Stereoselectivity Substrates |
| title | Lithium Hydroxide Assisted Endo‐Selective [4+4]‐Photocycloaddition of Pyran‐2‐ones |
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