Facile synthesis of 5-alkoxy-4-aryltetrahydrofuran-2-one using hypervalent iodine reagents
[Display omitted] γ-Lactones are used as building blocks in the synthesis of several naturally occurring products and biologically active compounds. In this work, a method of constructing a γ-lactone ring with an oxygen atom substituted at the γ position, with a short reaction time, mild reaction co...
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| Veröffentlicht in: | Tetrahedron letters 2023-03, Vol.118, p.154382, Article 154382 |
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| container_title | Tetrahedron letters |
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| creator | Matsumoto, Takuya Okazaki, Saya Aoki, Shui Niki, Aya Iwasaki, Hiroki Ozeki, Minoru Yamashita, Masayuki Kojima, Naoto Kawasaki, Ikuo |
| description | [Display omitted]
γ-Lactones are used as building blocks in the synthesis of several naturally occurring products and biologically active compounds. In this work, a method of constructing a γ-lactone ring with an oxygen atom substituted at the γ position, with a short reaction time, mild reaction conditions, simple operation, and stereoselectivity, was developed. Using this reaction, the synthesis of the γ-lactone ring with various substituents (mainly halogenated alkoxy groups) at the γ position is possible. |
| doi_str_mv | 10.1016/j.tetlet.2023.154382 |
| format | Article |
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γ-Lactones are used as building blocks in the synthesis of several naturally occurring products and biologically active compounds. In this work, a method of constructing a γ-lactone ring with an oxygen atom substituted at the γ position, with a short reaction time, mild reaction conditions, simple operation, and stereoselectivity, was developed. Using this reaction, the synthesis of the γ-lactone ring with various substituents (mainly halogenated alkoxy groups) at the γ position is possible.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2023.154382</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Acetal ; Hypervalent iodine (III) reagent ; iodine ; Lactonization ; oxygen ; Stereoselective ; stereoselectivity ; γ-Lactone</subject><ispartof>Tetrahedron letters, 2023-03, Vol.118, p.154382, Article 154382</ispartof><rights>2023 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c354t-669080316dc1c2cd6d45f15e1f213f5367a9d4e88e028d772be3ff58c39c10683</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040403923000564$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids></links><search><creatorcontrib>Matsumoto, Takuya</creatorcontrib><creatorcontrib>Okazaki, Saya</creatorcontrib><creatorcontrib>Aoki, Shui</creatorcontrib><creatorcontrib>Niki, Aya</creatorcontrib><creatorcontrib>Iwasaki, Hiroki</creatorcontrib><creatorcontrib>Ozeki, Minoru</creatorcontrib><creatorcontrib>Yamashita, Masayuki</creatorcontrib><creatorcontrib>Kojima, Naoto</creatorcontrib><creatorcontrib>Kawasaki, Ikuo</creatorcontrib><title>Facile synthesis of 5-alkoxy-4-aryltetrahydrofuran-2-one using hypervalent iodine reagents</title><title>Tetrahedron letters</title><description>[Display omitted]
γ-Lactones are used as building blocks in the synthesis of several naturally occurring products and biologically active compounds. In this work, a method of constructing a γ-lactone ring with an oxygen atom substituted at the γ position, with a short reaction time, mild reaction conditions, simple operation, and stereoselectivity, was developed. Using this reaction, the synthesis of the γ-lactone ring with various substituents (mainly halogenated alkoxy groups) at the γ position is possible.</description><subject>Acetal</subject><subject>Hypervalent iodine (III) reagent</subject><subject>iodine</subject><subject>Lactonization</subject><subject>oxygen</subject><subject>Stereoselective</subject><subject>stereoselectivity</subject><subject>γ-Lactone</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kD9PwzAQxS0EEqXwDRgysjjYcZw4CxKq-CdVYoGFxTL2uXVJ42K7Ffn2uAozt5xO996T3g-ha0pKSmhzuykTpB5SWZGKlZTXTFQnaEZFyzDjgp6iGSE1wTVh3Tm6iHFD8jSCzNDHo9KuhyKOQ1pDdLHwtuBY9V_-Z8Q1VmHsc3hQ69EEb_dBDbjCfoBiH92wKtbjDsJB9TCkwnnj8iOAWuUzXqIzq_oIV397jt4fH94Wz3j5-vSyuF9izXidcNN0RBBGG6OprrRpTM0t5UBtRZnlrGlVZ2oQAkglTNtWn8Cs5UKzTtNcgs3RzZS7C_57DzHJrYsa-l4N4PdRMspZ2zacsCytJ6kOPsYAVu6C2-aOkhJ5RCk3ckIpjyjlhDLb7iYb5BoHB0FG7WDQYFwAnaTx7v-AX24Wfyg</recordid><startdate>20230324</startdate><enddate>20230324</enddate><creator>Matsumoto, Takuya</creator><creator>Okazaki, Saya</creator><creator>Aoki, Shui</creator><creator>Niki, Aya</creator><creator>Iwasaki, Hiroki</creator><creator>Ozeki, Minoru</creator><creator>Yamashita, Masayuki</creator><creator>Kojima, Naoto</creator><creator>Kawasaki, Ikuo</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7S9</scope><scope>L.6</scope></search><sort><creationdate>20230324</creationdate><title>Facile synthesis of 5-alkoxy-4-aryltetrahydrofuran-2-one using hypervalent iodine reagents</title><author>Matsumoto, Takuya ; Okazaki, Saya ; Aoki, Shui ; Niki, Aya ; Iwasaki, Hiroki ; Ozeki, Minoru ; Yamashita, Masayuki ; Kojima, Naoto ; Kawasaki, Ikuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c354t-669080316dc1c2cd6d45f15e1f213f5367a9d4e88e028d772be3ff58c39c10683</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acetal</topic><topic>Hypervalent iodine (III) reagent</topic><topic>iodine</topic><topic>Lactonization</topic><topic>oxygen</topic><topic>Stereoselective</topic><topic>stereoselectivity</topic><topic>γ-Lactone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Matsumoto, Takuya</creatorcontrib><creatorcontrib>Okazaki, Saya</creatorcontrib><creatorcontrib>Aoki, Shui</creatorcontrib><creatorcontrib>Niki, Aya</creatorcontrib><creatorcontrib>Iwasaki, Hiroki</creatorcontrib><creatorcontrib>Ozeki, Minoru</creatorcontrib><creatorcontrib>Yamashita, Masayuki</creatorcontrib><creatorcontrib>Kojima, Naoto</creatorcontrib><creatorcontrib>Kawasaki, Ikuo</creatorcontrib><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Matsumoto, Takuya</au><au>Okazaki, Saya</au><au>Aoki, Shui</au><au>Niki, Aya</au><au>Iwasaki, Hiroki</au><au>Ozeki, Minoru</au><au>Yamashita, Masayuki</au><au>Kojima, Naoto</au><au>Kawasaki, Ikuo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Facile synthesis of 5-alkoxy-4-aryltetrahydrofuran-2-one using hypervalent iodine reagents</atitle><jtitle>Tetrahedron letters</jtitle><date>2023-03-24</date><risdate>2023</risdate><volume>118</volume><spage>154382</spage><pages>154382-</pages><artnum>154382</artnum><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>[Display omitted]
γ-Lactones are used as building blocks in the synthesis of several naturally occurring products and biologically active compounds. In this work, a method of constructing a γ-lactone ring with an oxygen atom substituted at the γ position, with a short reaction time, mild reaction conditions, simple operation, and stereoselectivity, was developed. Using this reaction, the synthesis of the γ-lactone ring with various substituents (mainly halogenated alkoxy groups) at the γ position is possible.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2023.154382</doi></addata></record> |
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| ispartof | Tetrahedron letters, 2023-03, Vol.118, p.154382, Article 154382 |
| issn | 0040-4039 1873-3581 |
| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Acetal Hypervalent iodine (III) reagent iodine Lactonization oxygen Stereoselective stereoselectivity γ-Lactone |
| title | Facile synthesis of 5-alkoxy-4-aryltetrahydrofuran-2-one using hypervalent iodine reagents |
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