Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines
A novel rearrangement of 2‐vinyl aziridine 2‐carboxylates to unusual chiral cyclic sulfoximines is described herein. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, and tolerates a wide substrate scope. A one‐pot process starting directl...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-08, Vol.55 (34), p.10047-10051 |
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| container_issue | 34 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Moragas, Toni Liffey, Ryan M. Regentová, Dominika Ward, Jon-Paul S. Dutton, Justine Lewis, William Churcher, Ian Walton, Lesley Souto, José A. Stockman, Robert A. |
| description | A novel rearrangement of 2‐vinyl aziridine 2‐carboxylates to unusual chiral cyclic sulfoximines is described herein. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, and tolerates a wide substrate scope. A one‐pot process starting directly from sulfinimines provides access to complex chiral sulfoximines in only two steps from commercially available aldehydes. A mechanistic hypothesis and synthetic application in the formal synthesis of trachelanthamidine, by transformation of a cyclic sulfoximine into a pyrroline, is also disclosed.
Making and breaking rings: A novel rearrangement of 2‐vinyl aziridine 2‐carboxylates to unusual chiral cyclic sulfoximines is described. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, and tolerates a wide substrate scope. A one‐pot process starting directly from sulfinimines provides access to complex chiral sulfoximines in only two steps from commercially available aldehydes. |
| doi_str_mv | 10.1002/anie.201604188 |
| format | Article |
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Making and breaking rings: A novel rearrangement of 2‐vinyl aziridine 2‐carboxylates to unusual chiral cyclic sulfoximines is described. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, and tolerates a wide substrate scope. A one‐pot process starting directly from sulfinimines provides access to complex chiral sulfoximines in only two steps from commercially available aldehydes.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201604188</identifier><identifier>PMID: 27409574</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>heterocycles ; rearrangements ; small ring compounds ; sulfur ; synthetic methods</subject><ispartof>Angewandte Chemie International Edition, 2016-08, Vol.55 (34), p.10047-10051</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5148-2d93b9139abffdaeaeae3eaa3b2d2b01a2f9f1087f7a3226ae1e90645d02aa63</citedby><cites>FETCH-LOGICAL-c5148-2d93b9139abffdaeaeae3eaa3b2d2b01a2f9f1087f7a3226ae1e90645d02aa63</cites><orcidid>0000-0002-7915-340X</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%2Fanie.201604188$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201604188$$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/27409574$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Moragas, Toni</creatorcontrib><creatorcontrib>Liffey, Ryan M.</creatorcontrib><creatorcontrib>Regentová, Dominika</creatorcontrib><creatorcontrib>Ward, Jon-Paul S.</creatorcontrib><creatorcontrib>Dutton, Justine</creatorcontrib><creatorcontrib>Lewis, William</creatorcontrib><creatorcontrib>Churcher, Ian</creatorcontrib><creatorcontrib>Walton, Lesley</creatorcontrib><creatorcontrib>Souto, José A.</creatorcontrib><creatorcontrib>Stockman, Robert A.</creatorcontrib><title>Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A novel rearrangement of 2‐vinyl aziridine 2‐carboxylates to unusual chiral cyclic sulfoximines is described herein. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, and tolerates a wide substrate scope. A one‐pot process starting directly from sulfinimines provides access to complex chiral sulfoximines in only two steps from commercially available aldehydes. A mechanistic hypothesis and synthetic application in the formal synthesis of trachelanthamidine, by transformation of a cyclic sulfoximine into a pyrroline, is also disclosed.
Making and breaking rings: A novel rearrangement of 2‐vinyl aziridine 2‐carboxylates to unusual chiral cyclic sulfoximines is described. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, and tolerates a wide substrate scope. A one‐pot process starting directly from sulfinimines provides access to complex chiral sulfoximines in only two steps from commercially available aldehydes.</description><subject>heterocycles</subject><subject>rearrangements</subject><subject>small ring compounds</subject><subject>sulfur</subject><subject>synthetic methods</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkc1v1DAQxS0EoqVw5YgiceGSxV-JbW6r1XaptCoqW1GJi-Uk49YlcRY7UTf89SSkrFAvaA4e6f3e08gPobcELwjG9KPxDhYUkxxzIuUzdEoySlImBHs-7pyxVMiMnKBXMd6PvJQ4f4lOqOBYZYKforBzt43pQrt3ZfIVTAjG30IDvktam3xzfqiT5S8XXOU8xE_J-rCHyk3ybvDdHUQXJ3A1lPUYsOtr2x5cM7GJDW2TrO5cMPUfwflZeI1eWFNHePP4nqHr8_X16nO6_bK5WC23aZkRLlNaKVYowpQprK0MTMPAGFbQihaYGGqVJVgKKwyjNDdAQOGcZxWmxuTsDH2YY_eh_dlD7HTjYgl1bTy0fdREEpxlSuR8RN8_Qe_bPvjxuIkiivJMTtRipsrQxhjA6n1wjQmDJlhPZeipDH0sYzS8e4ztiwaqI_7390dAzcCDq2H4T5xeXl6s_w1PZ6-LHRyOXhN-6Fwwkemby42-4eIq_77FesN-A_eNp04</recordid><startdate>20160816</startdate><enddate>20160816</enddate><creator>Moragas, Toni</creator><creator>Liffey, Ryan M.</creator><creator>Regentová, Dominika</creator><creator>Ward, Jon-Paul S.</creator><creator>Dutton, Justine</creator><creator>Lewis, William</creator><creator>Churcher, Ian</creator><creator>Walton, Lesley</creator><creator>Souto, José A.</creator><creator>Stockman, Robert A.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7915-340X</orcidid></search><sort><creationdate>20160816</creationdate><title>Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines</title><author>Moragas, Toni ; Liffey, Ryan M. ; Regentová, Dominika ; Ward, Jon-Paul S. ; Dutton, Justine ; Lewis, William ; Churcher, Ian ; Walton, Lesley ; Souto, José A. ; Stockman, Robert A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5148-2d93b9139abffdaeaeae3eaa3b2d2b01a2f9f1087f7a3226ae1e90645d02aa63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>heterocycles</topic><topic>rearrangements</topic><topic>small ring compounds</topic><topic>sulfur</topic><topic>synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Moragas, Toni</creatorcontrib><creatorcontrib>Liffey, Ryan M.</creatorcontrib><creatorcontrib>Regentová, Dominika</creatorcontrib><creatorcontrib>Ward, Jon-Paul S.</creatorcontrib><creatorcontrib>Dutton, Justine</creatorcontrib><creatorcontrib>Lewis, William</creatorcontrib><creatorcontrib>Churcher, Ian</creatorcontrib><creatorcontrib>Walton, Lesley</creatorcontrib><creatorcontrib>Souto, José A.</creatorcontrib><creatorcontrib>Stockman, Robert A.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Moragas, Toni</au><au>Liffey, Ryan M.</au><au>Regentová, Dominika</au><au>Ward, Jon-Paul S.</au><au>Dutton, Justine</au><au>Lewis, William</au><au>Churcher, Ian</au><au>Walton, Lesley</au><au>Souto, José A.</au><au>Stockman, Robert A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-08-16</date><risdate>2016</risdate><volume>55</volume><issue>34</issue><spage>10047</spage><epage>10051</epage><pages>10047-10051</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A novel rearrangement of 2‐vinyl aziridine 2‐carboxylates to unusual chiral cyclic sulfoximines is described herein. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, and tolerates a wide substrate scope. A one‐pot process starting directly from sulfinimines provides access to complex chiral sulfoximines in only two steps from commercially available aldehydes. A mechanistic hypothesis and synthetic application in the formal synthesis of trachelanthamidine, by transformation of a cyclic sulfoximine into a pyrroline, is also disclosed.
Making and breaking rings: A novel rearrangement of 2‐vinyl aziridine 2‐carboxylates to unusual chiral cyclic sulfoximines is described. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, and tolerates a wide substrate scope. A one‐pot process starting directly from sulfinimines provides access to complex chiral sulfoximines in only two steps from commercially available aldehydes.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27409574</pmid><doi>10.1002/anie.201604188</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-7915-340X</orcidid></addata></record> |
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| subjects | heterocycles rearrangements small ring compounds sulfur synthetic methods |
| title | Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines |
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