Modulating Prins Cyclization versus Tandem Prins Processes for the Synthesis of Hexahydro‐1H‐pyrano[3,4‐c]chromenes
We propose the synthesis of biologically relevant hexahydro‐1H‐pyrano[3,4‐c]chromenes, via a tandem Prins/Friedels‐Crafts process, catalyzed by BF3.Et2O, starting from (E)‐ and (Z)‐5‐phenoxypent‐3‐en‐1‐ol. The diastereoselectivity of the process is controlled by the geometry of the homoallylic alcoh...
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| Veröffentlicht in: | European journal of organic chemistry 2021-01, Vol.2021 (1), p.138-145 |
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| container_title | European journal of organic chemistry |
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| creator | Satteyyanaidu, Vallabhareddy Chandrashekhar, Rapelli Reddy, B. V. Subba Lalli, Claudia |
| description | We propose the synthesis of biologically relevant hexahydro‐1H‐pyrano[3,4‐c]chromenes, via a tandem Prins/Friedels‐Crafts process, catalyzed by BF3.Et2O, starting from (E)‐ and (Z)‐5‐phenoxypent‐3‐en‐1‐ol. The diastereoselectivity of the process is controlled by the geometry of the homoallylic alcohol. We also point out that the Prins product can be obtained in high yields and good diastereoselectivity when the reaction is promoted by AlCl3 as Lewis acid in the presence of an external nucleophile.
By varying the conditions of the reaction between (E)‐ or (Z)‐5‐phenoxypent‐3‐en‐1‐ol and aldehydes, we can either access biologically relevant hexahydro‐1H‐pyrano[3,4‐c]chromenes via a tandem Prins/Friedel‐Crafts cascade or the tetrahydropyrane intermediate of the Prins process. In both cases, the products are obtained in high yields and good diastereoselectivities. |
| doi_str_mv | 10.1002/ejoc.202000220 |
| format | Article |
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By varying the conditions of the reaction between (E)‐ or (Z)‐5‐phenoxypent‐3‐en‐1‐ol and aldehydes, we can either access biologically relevant hexahydro‐1H‐pyrano[3,4‐c]chromenes via a tandem Prins/Friedel‐Crafts cascade or the tetrahydropyrane intermediate of the Prins process. In both cases, the products are obtained in high yields and good diastereoselectivities.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202000220</identifier><language>eng</language><publisher>Wiley-VCH Verlag</publisher><subject>Chemical Sciences ; Organic chemistry ; Oxygen heterocycles ; Prins cyclization ; Synthetic methods ; Tandem processes</subject><ispartof>European journal of organic chemistry, 2021-01, Vol.2021 (1), p.138-145</ispartof><rights>2020 Wiley‐VCH GmbH</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-1634-716X</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.202000220$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202000220$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,776,780,881,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://hal.science/hal-03100379$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Satteyyanaidu, Vallabhareddy</creatorcontrib><creatorcontrib>Chandrashekhar, Rapelli</creatorcontrib><creatorcontrib>Reddy, B. V. Subba</creatorcontrib><creatorcontrib>Lalli, Claudia</creatorcontrib><title>Modulating Prins Cyclization versus Tandem Prins Processes for the Synthesis of Hexahydro‐1H‐pyrano[3,4‐c]chromenes</title><title>European journal of organic chemistry</title><description>We propose the synthesis of biologically relevant hexahydro‐1H‐pyrano[3,4‐c]chromenes, via a tandem Prins/Friedels‐Crafts process, catalyzed by BF3.Et2O, starting from (E)‐ and (Z)‐5‐phenoxypent‐3‐en‐1‐ol. The diastereoselectivity of the process is controlled by the geometry of the homoallylic alcohol. We also point out that the Prins product can be obtained in high yields and good diastereoselectivity when the reaction is promoted by AlCl3 as Lewis acid in the presence of an external nucleophile.
By varying the conditions of the reaction between (E)‐ or (Z)‐5‐phenoxypent‐3‐en‐1‐ol and aldehydes, we can either access biologically relevant hexahydro‐1H‐pyrano[3,4‐c]chromenes via a tandem Prins/Friedel‐Crafts cascade or the tetrahydropyrane intermediate of the Prins process. In both cases, the products are obtained in high yields and good diastereoselectivities.</description><subject>Chemical Sciences</subject><subject>Organic chemistry</subject><subject>Oxygen heterocycles</subject><subject>Prins cyclization</subject><subject>Synthetic methods</subject><subject>Tandem processes</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNo9kEFLw0AQhYMoWKtXz3sVTJ3NppvssZRqlEoLVhBElu1mYlLSbNltq_HkT_A3-kvcYull3rw3H3N4QXBJoUcBohtcGN2LIAJvIjgKOhSECIELOPZ7zOKQCvZyGpw5t_CM4Jx2gvbR5JtaravmnUxt1TgybHVdffnENGSL1m0cmakmx-X-PrVGo3PoSGEsWZdIntrGi6scMQXJ8FOVbW7N7_cPzfxYtVY15pVdx97oN11as8QG3XlwUqja4cVeu8Hz7Wg2zMLx5O5-OBiHZZQICItkzjRLdIy0j1r3OYNcM4xFn6MSkOaQsxhTYJGKOfA5S2nKRcITHlFWYM66wdX_31LVcmWrpbKtNKqS2WAsdxkwXx9LxJZ6VvyzH1WN7YGmIHcNy13D8tCwHD1MhgfH_gBdN3WH</recordid><startdate>20210108</startdate><enddate>20210108</enddate><creator>Satteyyanaidu, Vallabhareddy</creator><creator>Chandrashekhar, Rapelli</creator><creator>Reddy, B. V. Subba</creator><creator>Lalli, Claudia</creator><general>Wiley-VCH Verlag</general><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-1634-716X</orcidid></search><sort><creationdate>20210108</creationdate><title>Modulating Prins Cyclization versus Tandem Prins Processes for the Synthesis of Hexahydro‐1H‐pyrano[3,4‐c]chromenes</title><author>Satteyyanaidu, Vallabhareddy ; Chandrashekhar, Rapelli ; Reddy, B. V. Subba ; Lalli, Claudia</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-h2790-f7b3c37c4e15ecc5630dc3e4956ea908d0d34e8032a4606b3818697676213fed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Chemical Sciences</topic><topic>Organic chemistry</topic><topic>Oxygen heterocycles</topic><topic>Prins cyclization</topic><topic>Synthetic methods</topic><topic>Tandem processes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Satteyyanaidu, Vallabhareddy</creatorcontrib><creatorcontrib>Chandrashekhar, Rapelli</creatorcontrib><creatorcontrib>Reddy, B. V. Subba</creatorcontrib><creatorcontrib>Lalli, Claudia</creatorcontrib><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Satteyyanaidu, Vallabhareddy</au><au>Chandrashekhar, Rapelli</au><au>Reddy, B. V. Subba</au><au>Lalli, Claudia</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Modulating Prins Cyclization versus Tandem Prins Processes for the Synthesis of Hexahydro‐1H‐pyrano[3,4‐c]chromenes</atitle><jtitle>European journal of organic chemistry</jtitle><date>2021-01-08</date><risdate>2021</risdate><volume>2021</volume><issue>1</issue><spage>138</spage><epage>145</epage><pages>138-145</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>We propose the synthesis of biologically relevant hexahydro‐1H‐pyrano[3,4‐c]chromenes, via a tandem Prins/Friedels‐Crafts process, catalyzed by BF3.Et2O, starting from (E)‐ and (Z)‐5‐phenoxypent‐3‐en‐1‐ol. The diastereoselectivity of the process is controlled by the geometry of the homoallylic alcohol. We also point out that the Prins product can be obtained in high yields and good diastereoselectivity when the reaction is promoted by AlCl3 as Lewis acid in the presence of an external nucleophile.
By varying the conditions of the reaction between (E)‐ or (Z)‐5‐phenoxypent‐3‐en‐1‐ol and aldehydes, we can either access biologically relevant hexahydro‐1H‐pyrano[3,4‐c]chromenes via a tandem Prins/Friedel‐Crafts cascade or the tetrahydropyrane intermediate of the Prins process. In both cases, the products are obtained in high yields and good diastereoselectivities.</abstract><pub>Wiley-VCH Verlag</pub><doi>10.1002/ejoc.202000220</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-1634-716X</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | European journal of organic chemistry, 2021-01, Vol.2021 (1), p.138-145 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Chemical Sciences Organic chemistry Oxygen heterocycles Prins cyclization Synthetic methods Tandem processes |
| title | Modulating Prins Cyclization versus Tandem Prins Processes for the Synthesis of Hexahydro‐1H‐pyrano[3,4‐c]chromenes |
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