Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center
An enantio‐, diastereo‐, regio‐, and chemoselective phosphine‐catalyzed β,γ‐umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence, involving oxy‐Michael and Rauhut–Currier reactions, produced highly functionalized tetrahydrobenzofuranon...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-12, Vol.54 (51), p.15511-15515 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Takizawa, Shinobu Kishi, Kenta Yoshida, Yasushi Mader, Steffen Arteaga, Fernando Arteaga Lee, Shoukou Hoshino, Manabu Rueping, Magnus Fujita, Makoto Sasai, Hiroaki |
| description | An enantio‐, diastereo‐, regio‐, and chemoselective phosphine‐catalyzed β,γ‐umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence, involving oxy‐Michael and Rauhut–Currier reactions, produced highly functionalized tetrahydrobenzofuranones, bearing a chiral tetrasubstituted stereogenic center, in up to 96 % ee.
Domino effect: An enantio‐, diastereo‐, regio‐, and chemoselective phosphine‐catalyzed β,γ‐umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence involving oxy‐Michael and Rauhut–Currier reactions produced highly functionalized tetrahydrobenzofuranones bearing a chiral tetrasubstituted stereogenic center in up to 96 % ee. |
| doi_str_mv | 10.1002/anie.201508022 |
| format | Article |
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Domino effect: An enantio‐, diastereo‐, regio‐, and chemoselective phosphine‐catalyzed β,γ‐umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence involving oxy‐Michael and Rauhut–Currier reactions produced highly functionalized tetrahydrobenzofuranones bearing a chiral tetrasubstituted stereogenic center in up to 96 % ee.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201508022</identifier><identifier>PMID: 26537173</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>allenes ; annulations ; Cascade chemical reactions ; Esters ; organocatalysis ; Phosphine ; Phosphines ; umpolung</subject><ispartof>Angewandte Chemie International Edition, 2015-12, Vol.54 (51), p.15511-15515</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright Wiley Subscription Services, Inc. Dec 2015</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4812-bb8160513bd8cb30bfdee68f5731dac7ee11b22e0318d718404f1772c34f91a33</citedby><cites>FETCH-LOGICAL-c4812-bb8160513bd8cb30bfdee68f5731dac7ee11b22e0318d718404f1772c34f91a33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201508022$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201508022$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26537173$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Takizawa, Shinobu</creatorcontrib><creatorcontrib>Kishi, Kenta</creatorcontrib><creatorcontrib>Yoshida, Yasushi</creatorcontrib><creatorcontrib>Mader, Steffen</creatorcontrib><creatorcontrib>Arteaga, Fernando Arteaga</creatorcontrib><creatorcontrib>Lee, Shoukou</creatorcontrib><creatorcontrib>Hoshino, Manabu</creatorcontrib><creatorcontrib>Rueping, Magnus</creatorcontrib><creatorcontrib>Fujita, Makoto</creatorcontrib><creatorcontrib>Sasai, Hiroaki</creatorcontrib><title>Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>An enantio‐, diastereo‐, regio‐, and chemoselective phosphine‐catalyzed β,γ‐umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence, involving oxy‐Michael and Rauhut–Currier reactions, produced highly functionalized tetrahydrobenzofuranones, bearing a chiral tetrasubstituted stereogenic center, in up to 96 % ee.
Domino effect: An enantio‐, diastereo‐, regio‐, and chemoselective phosphine‐catalyzed β,γ‐umpolung domino reaction of allenic esters with dienones has been developed for the first time. 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Domino effect: An enantio‐, diastereo‐, regio‐, and chemoselective phosphine‐catalyzed β,γ‐umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence involving oxy‐Michael and Rauhut–Currier reactions produced highly functionalized tetrahydrobenzofuranones bearing a chiral tetrasubstituted stereogenic center in up to 96 % ee.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26537173</pmid><doi>10.1002/anie.201508022</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | allenes annulations Cascade chemical reactions Esters organocatalysis Phosphine Phosphines umpolung |
| title | Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center |
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