One-step Preparation of N-Unprotected Aziridines from 2H-Azirines by Addition of Ketene Silyl Acetals Catalyzed by Lewis Acids
The nucleophilic addition of ketene silyl acetals 2 into 2H-azirines 1 proceeded in the presence of Lewis acids such as InX3 or Sc(OTf)3 to give N-unprotected aziridines 3. The mild Lewis acidity of the catalyst is important for the achievement of this coupling. The generated aziridine 3 could then...
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Veröffentlicht in: | Chemistry letters 2022-01, Vol.51 (1), p.9-12 |
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creator | Suzuki, Itaru Takenaka, Yuya Morishita, Yoshitaka Shibata, Ikuya |
description | The nucleophilic addition of ketene silyl acetals 2 into 2H-azirines 1 proceeded in the presence of Lewis acids such as InX3 or Sc(OTf)3 to give N-unprotected aziridines 3. The mild Lewis acidity of the catalyst is important for the achievement of this coupling. The generated aziridine 3 could then be transformed into either oxazolines or γ–amino carbonyls. |
doi_str_mv | 10.1246/cl.210589 |
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The mild Lewis acidity of the catalyst is important for the achievement of this coupling. The generated aziridine 3 could then be transformed into either oxazolines or γ–amino carbonyls.</description><identifier>ISSN: 0366-7022</identifier><identifier>EISSN: 1348-0715</identifier><identifier>DOI: 10.1246/cl.210589</identifier><language>eng</language><publisher>Tokyo: The Chemical Society of Japan</publisher><subject>Acetals ; Carbonyls</subject><ispartof>Chemistry letters, 2022-01, Vol.51 (1), p.9-12</ispartof><rights>The Chemical Society of Japan</rights><rights>Copyright Chemical Society of Japan 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Suzuki, Itaru</creatorcontrib><creatorcontrib>Takenaka, Yuya</creatorcontrib><creatorcontrib>Morishita, Yoshitaka</creatorcontrib><creatorcontrib>Shibata, Ikuya</creatorcontrib><title>One-step Preparation of N-Unprotected Aziridines from 2H-Azirines by Addition of Ketene Silyl Acetals Catalyzed by Lewis Acids</title><title>Chemistry letters</title><description>The nucleophilic addition of ketene silyl acetals 2 into 2H-azirines 1 proceeded in the presence of Lewis acids such as InX3 or Sc(OTf)3 to give N-unprotected aziridines 3. The mild Lewis acidity of the catalyst is important for the achievement of this coupling. The generated aziridine 3 could then be transformed into either oxazolines or γ–amino carbonyls.</description><subject>Acetals</subject><subject>Carbonyls</subject><issn>0366-7022</issn><issn>1348-0715</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpFUE1LwzAYDqLgnB78BwHPmflOeyxDnTicoDuXNE0wo2trkyHdwd9u5hRPDzxfL-8DwDXBM0K5vDXNjBIssvwETAjjGcKKiFMwwUxKpDCl5-AihA3GOMsZnYCvVWtRiLaHL4Pt9aCj71rYOfiM1m0_dNGaaGtY7P3ga9_aAN3QbSFdoB_qQFQjLOra_wWfbLStha--GRtYGBt1E-BcJxj3qSm5l_bThyT5OlyCM5d0e_WLU7C-v3ubL9By9fA4L5bI0FxGxHWW0ZxrzZzCvFJGOlIxplWlqGOCMGEq5XAthCQsYzIXXBKjOFFG8AoLNgU3x9700sfOhlhuut3QppMllUSoFKR5csmjy7zbrTdJ7Yy3cdzoXrf_CYLLw9alacrj1uwbtQhxYw</recordid><startdate>20220101</startdate><enddate>20220101</enddate><creator>Suzuki, Itaru</creator><creator>Takenaka, Yuya</creator><creator>Morishita, Yoshitaka</creator><creator>Shibata, Ikuya</creator><general>The Chemical Society of Japan</general><general>Chemical Society of Japan</general><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20220101</creationdate><title>One-step Preparation of N-Unprotected Aziridines from 2H-Azirines by Addition of Ketene Silyl Acetals Catalyzed by Lewis Acids</title><author>Suzuki, Itaru ; Takenaka, Yuya ; Morishita, Yoshitaka ; Shibata, Ikuya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-4a88294aa3f704b7c6f1b33a7b72f35135cb7f0d5561383695461c7417c54b053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Acetals</topic><topic>Carbonyls</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Suzuki, Itaru</creatorcontrib><creatorcontrib>Takenaka, Yuya</creatorcontrib><creatorcontrib>Morishita, Yoshitaka</creatorcontrib><creatorcontrib>Shibata, Ikuya</creatorcontrib><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Suzuki, Itaru</au><au>Takenaka, Yuya</au><au>Morishita, Yoshitaka</au><au>Shibata, Ikuya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-step Preparation of N-Unprotected Aziridines from 2H-Azirines by Addition of Ketene Silyl Acetals Catalyzed by Lewis Acids</atitle><jtitle>Chemistry letters</jtitle><date>2022-01-01</date><risdate>2022</risdate><volume>51</volume><issue>1</issue><spage>9</spage><epage>12</epage><pages>9-12</pages><issn>0366-7022</issn><eissn>1348-0715</eissn><abstract>The nucleophilic addition of ketene silyl acetals 2 into 2H-azirines 1 proceeded in the presence of Lewis acids such as InX3 or Sc(OTf)3 to give N-unprotected aziridines 3. The mild Lewis acidity of the catalyst is important for the achievement of this coupling. The generated aziridine 3 could then be transformed into either oxazolines or γ–amino carbonyls.</abstract><cop>Tokyo</cop><pub>The Chemical Society of Japan</pub><doi>10.1246/cl.210589</doi><tpages>4</tpages></addata></record> |
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source | Oxford University Press Journals All Titles (1996-Current) |
subjects | Acetals Carbonyls |
title | One-step Preparation of N-Unprotected Aziridines from 2H-Azirines by Addition of Ketene Silyl Acetals Catalyzed by Lewis Acids |
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