Synthesis of 1‐Aminoindenes through Aza‐Prins‐Type Cyclization
An acid‐catalyzed aza‐Prins‐type endo cyclization of 2‐alkenylbenzaldehydes with BocNH2 or aniline derivatives through in situ generation of iminium intermediates has been developed, and various 1‐aminoindene derivatives were readily obtained. The first catalytic asymmetric variant of the present re...
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| Veröffentlicht in: | Chemistry : a European journal 2018-07, Vol.24 (41), p.10320-10323 |
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| container_title | Chemistry : a European journal |
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| creator | Bai, Jian‐Fei Yasumoto, Kento Kano, Taichi Maruoka, Keiji |
| description | An acid‐catalyzed aza‐Prins‐type endo cyclization of 2‐alkenylbenzaldehydes with BocNH2 or aniline derivatives through in situ generation of iminium intermediates has been developed, and various 1‐aminoindene derivatives were readily obtained. The first catalytic asymmetric variant of the present reaction has also been demonstrated.
endo Cyclization: An acid‐catalyzed aza‐Prins‐type endo cyclization of 2‐alkenylbenzaldehydes with BocNH2 or aniline derivatives through in situ generation of iminium intermediates has been developed, and various 1‐aminoindene derivatives were readily obtained. The first catalytic asymmetric variant of the present reaction has also been demonstrated (see scheme). |
| doi_str_mv | 10.1002/chem.201802448 |
| format | Article |
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endo Cyclization: An acid‐catalyzed aza‐Prins‐type endo cyclization of 2‐alkenylbenzaldehydes with BocNH2 or aniline derivatives through in situ generation of iminium intermediates has been developed, and various 1‐aminoindene derivatives were readily obtained. The first catalytic asymmetric variant of the present reaction has also been demonstrated (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201802448</identifier><identifier>PMID: 29802655</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>amines ; Aniline ; asymmetric catalysis ; Brønsted acids ; Catalysis ; Chemical synthesis ; Chemistry ; cyclization ; Derivatives ; imines ; Intermediates</subject><ispartof>Chemistry : a European journal, 2018-07, Vol.24 (41), p.10320-10323</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4768-83aa7228b63966edce366dca4d6035e671efa6d96b14b6d3a0b6ad5a1d2d61f33</citedby><cites>FETCH-LOGICAL-c4768-83aa7228b63966edce366dca4d6035e671efa6d96b14b6d3a0b6ad5a1d2d61f33</cites><orcidid>0000-0002-0044-6411</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%2Fchem.201802448$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201802448$$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/29802655$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bai, Jian‐Fei</creatorcontrib><creatorcontrib>Yasumoto, Kento</creatorcontrib><creatorcontrib>Kano, Taichi</creatorcontrib><creatorcontrib>Maruoka, Keiji</creatorcontrib><title>Synthesis of 1‐Aminoindenes through Aza‐Prins‐Type Cyclization</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>An acid‐catalyzed aza‐Prins‐type endo cyclization of 2‐alkenylbenzaldehydes with BocNH2 or aniline derivatives through in situ generation of iminium intermediates has been developed, and various 1‐aminoindene derivatives were readily obtained. The first catalytic asymmetric variant of the present reaction has also been demonstrated.
endo Cyclization: An acid‐catalyzed aza‐Prins‐type endo cyclization of 2‐alkenylbenzaldehydes with BocNH2 or aniline derivatives through in situ generation of iminium intermediates has been developed, and various 1‐aminoindene derivatives were readily obtained. The first catalytic asymmetric variant of the present reaction has also been demonstrated (see scheme).</description><subject>amines</subject><subject>Aniline</subject><subject>asymmetric catalysis</subject><subject>Brønsted acids</subject><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>cyclization</subject><subject>Derivatives</subject><subject>imines</subject><subject>Intermediates</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqF0MtKw0AUBuBBFFurW5cScOMmdS6ZM8my1GqFioJ1HSaZiZ2SS80kSLryEXxGn8QprRXcuDqL852fw4_QOcFDgjG9The6GFJMQkyDIDxAfcIp8ZkAfoj6OAqED5xFPXRi7RJjHAFjx6hHI-eB8z66ee7KZqGtsV6VeeTr43NUmLIypdKltl6zqKv2deGN1tKtnmpTWjfn3Up74y7NzVo2pipP0VEmc6vPdnOAXm4n8_HUnz3e3Y9HMz8NBIR-yKQUlIYJsAhAq1QzAJXKQAFmXIMgOpOgIkhIkIBiEicgFZdEUQUkY2yArra5q7p6a7Vt4sLYVOe5LHXV2pjigFNBAAtHL__QZdXWpfvOKcFoQLDgTg23Kq0ra2udxavaFLLuYoLjTb_xpt943687uNjFtkmh1Z7_FOpAtAXvJtfdP3HxeDp5-A3_Bn6DiRw</recordid><startdate>20180720</startdate><enddate>20180720</enddate><creator>Bai, Jian‐Fei</creator><creator>Yasumoto, Kento</creator><creator>Kano, Taichi</creator><creator>Maruoka, Keiji</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-0044-6411</orcidid></search><sort><creationdate>20180720</creationdate><title>Synthesis of 1‐Aminoindenes through Aza‐Prins‐Type Cyclization</title><author>Bai, Jian‐Fei ; Yasumoto, Kento ; Kano, Taichi ; Maruoka, Keiji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4768-83aa7228b63966edce366dca4d6035e671efa6d96b14b6d3a0b6ad5a1d2d61f33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>amines</topic><topic>Aniline</topic><topic>asymmetric catalysis</topic><topic>Brønsted acids</topic><topic>Catalysis</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>cyclization</topic><topic>Derivatives</topic><topic>imines</topic><topic>Intermediates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bai, Jian‐Fei</creatorcontrib><creatorcontrib>Yasumoto, Kento</creatorcontrib><creatorcontrib>Kano, Taichi</creatorcontrib><creatorcontrib>Maruoka, Keiji</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bai, Jian‐Fei</au><au>Yasumoto, Kento</au><au>Kano, Taichi</au><au>Maruoka, Keiji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 1‐Aminoindenes through Aza‐Prins‐Type Cyclization</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2018-07-20</date><risdate>2018</risdate><volume>24</volume><issue>41</issue><spage>10320</spage><epage>10323</epage><pages>10320-10323</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>An acid‐catalyzed aza‐Prins‐type endo cyclization of 2‐alkenylbenzaldehydes with BocNH2 or aniline derivatives through in situ generation of iminium intermediates has been developed, and various 1‐aminoindene derivatives were readily obtained. The first catalytic asymmetric variant of the present reaction has also been demonstrated.
endo Cyclization: An acid‐catalyzed aza‐Prins‐type endo cyclization of 2‐alkenylbenzaldehydes with BocNH2 or aniline derivatives through in situ generation of iminium intermediates has been developed, and various 1‐aminoindene derivatives were readily obtained. The first catalytic asymmetric variant of the present reaction has also been demonstrated (see scheme).</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29802655</pmid><doi>10.1002/chem.201802448</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-0044-6411</orcidid></addata></record> |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | amines Aniline asymmetric catalysis Brønsted acids Catalysis Chemical synthesis Chemistry cyclization Derivatives imines Intermediates |
| title | Synthesis of 1‐Aminoindenes through Aza‐Prins‐Type Cyclization |
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