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Synergistic Catalysis: Enantioselective Addition of Alkylbenzoxazoles to Enals
A novel catalytic enantioselective methodology based on synergistic catalysis is reported. The strategy involves: 1) the metal‐Lewis‐acid activation of alkylazaarenes, and 2) the secondary‐amine activation of enals. Consequently, highly functionalized chiral alkylazaarenes were obtained in good yiel...
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Published in: | Chemistry : a European journal 2014-12, Vol.20 (51), p.16853-16857 |
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container_end_page | 16857 |
container_issue | 51 |
container_start_page | 16853 |
container_title | Chemistry : a European journal |
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creator | Meazza, Marta Ceban, Victor Pitak, Mateusz B. Coles, Simon J. Rios, Ramon |
description | A novel catalytic enantioselective methodology based on synergistic catalysis is reported. The strategy involves: 1) the metal‐Lewis‐acid activation of alkylazaarenes, and 2) the secondary‐amine activation of enals. Consequently, highly functionalized chiral alkylazaarenes were obtained in good yields and with reasonable stereoselectivity.
In good company: A novel catalytic enantioselective methodology based on synergistic catalysis is reported. The strategy involves: 1) the metal‐Lewis‐acid activation of alkylazaarenes, and 2) the secondary‐amine activation of enals (see scheme). Consequently, highly functionalized chiral alkylazaarenes were obtained in good yields and with reasonable stereoselectivity. |
doi_str_mv | 10.1002/chem.201404565 |
format | article |
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In good company: A novel catalytic enantioselective methodology based on synergistic catalysis is reported. The strategy involves: 1) the metal‐Lewis‐acid activation of alkylazaarenes, and 2) the secondary‐amine activation of enals (see scheme). Consequently, highly functionalized chiral alkylazaarenes were obtained in good yields and with reasonable stereoselectivity.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201404565</identifier><identifier>PMID: 25352171</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Activation ; alkyl azaarenes ; Catalysis ; Catalysts ; Chemistry ; iminium catalysis ; Methodology ; Michael addition ; palladium ; Stereoselectivity ; Strategy ; synergistic catalysis</subject><ispartof>Chemistry : a European journal, 2014-12, Vol.20 (51), p.16853-16857</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5875-d69cf486acee9e40740f46879178a6396fc8d6d9245e90c3df06e6a4b65b23fe3</citedby><cites>FETCH-LOGICAL-c5875-d69cf486acee9e40740f46879178a6396fc8d6d9245e90c3df06e6a4b65b23fe3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25352171$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Meazza, Marta</creatorcontrib><creatorcontrib>Ceban, Victor</creatorcontrib><creatorcontrib>Pitak, Mateusz B.</creatorcontrib><creatorcontrib>Coles, Simon J.</creatorcontrib><creatorcontrib>Rios, Ramon</creatorcontrib><title>Synergistic Catalysis: Enantioselective Addition of Alkylbenzoxazoles to Enals</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A novel catalytic enantioselective methodology based on synergistic catalysis is reported. The strategy involves: 1) the metal‐Lewis‐acid activation of alkylazaarenes, and 2) the secondary‐amine activation of enals. Consequently, highly functionalized chiral alkylazaarenes were obtained in good yields and with reasonable stereoselectivity.
In good company: A novel catalytic enantioselective methodology based on synergistic catalysis is reported. The strategy involves: 1) the metal‐Lewis‐acid activation of alkylazaarenes, and 2) the secondary‐amine activation of enals (see scheme). Consequently, highly functionalized chiral alkylazaarenes were obtained in good yields and with reasonable stereoselectivity.</description><subject>Activation</subject><subject>alkyl azaarenes</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>iminium catalysis</subject><subject>Methodology</subject><subject>Michael addition</subject><subject>palladium</subject><subject>Stereoselectivity</subject><subject>Strategy</subject><subject>synergistic catalysis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkc1v0zAYhy0EYmVw5YgiceGS4s_XMbdSSodUhsRAHC3XeQPe3HjEKSz760nUUSEuO72S9fweyXoIec7onFHKX_sfuJtzyiSVCtQDMmOKs1JoUA_JjBqpS1DCnJAnOV9SSg0I8ZiccCVGTLMZOb8YWuy-h9wHXyxd7-KQQ35TrFrX9iFljOj78AuLRV2H8aEtUlMs4tUQt9jepht3myLmok_TIuan5FEzHnx2d0_J1_erL8uzcvNp_WG52JReVVqVNRjfyAqcRzQoqZa0kVBpw3TlQBhofFVDbbhUaKgXdUMBwcktqC0XDYpT8urgve7Szz3m3u5C9hijazHtsx09wAw3nN-PgpBcSyMm9OV_6GXad9O_JoqySgFlIzU_UL5LOXfY2Osu7Fw3WEbtFMVOUewxyjh4cafdb3dYH_G_FUbAHIDfIeJwj84uz1Yf_5WXh-2YEG-OW9ddWdBCK_vtfG3VhVi_-_x2YyvxB3Sopuc</recordid><startdate>20141215</startdate><enddate>20141215</enddate><creator>Meazza, Marta</creator><creator>Ceban, Victor</creator><creator>Pitak, Mateusz B.</creator><creator>Coles, Simon J.</creator><creator>Rios, Ramon</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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></search><sort><creationdate>20141215</creationdate><title>Synergistic Catalysis: Enantioselective Addition of Alkylbenzoxazoles to Enals</title><author>Meazza, Marta ; Ceban, Victor ; Pitak, Mateusz B. ; Coles, Simon J. ; Rios, Ramon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5875-d69cf486acee9e40740f46879178a6396fc8d6d9245e90c3df06e6a4b65b23fe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Activation</topic><topic>alkyl azaarenes</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>iminium catalysis</topic><topic>Methodology</topic><topic>Michael addition</topic><topic>palladium</topic><topic>Stereoselectivity</topic><topic>Strategy</topic><topic>synergistic catalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Meazza, Marta</creatorcontrib><creatorcontrib>Ceban, Victor</creatorcontrib><creatorcontrib>Pitak, Mateusz B.</creatorcontrib><creatorcontrib>Coles, Simon J.</creatorcontrib><creatorcontrib>Rios, Ramon</creatorcontrib><collection>Istex</collection><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>Meazza, Marta</au><au>Ceban, Victor</au><au>Pitak, Mateusz B.</au><au>Coles, Simon J.</au><au>Rios, Ramon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synergistic Catalysis: Enantioselective Addition of Alkylbenzoxazoles to Enals</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2014-12-15</date><risdate>2014</risdate><volume>20</volume><issue>51</issue><spage>16853</spage><epage>16857</epage><pages>16853-16857</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A novel catalytic enantioselective methodology based on synergistic catalysis is reported. The strategy involves: 1) the metal‐Lewis‐acid activation of alkylazaarenes, and 2) the secondary‐amine activation of enals. Consequently, highly functionalized chiral alkylazaarenes were obtained in good yields and with reasonable stereoselectivity.
In good company: A novel catalytic enantioselective methodology based on synergistic catalysis is reported. The strategy involves: 1) the metal‐Lewis‐acid activation of alkylazaarenes, and 2) the secondary‐amine activation of enals (see scheme). Consequently, highly functionalized chiral alkylazaarenes were obtained in good yields and with reasonable stereoselectivity.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25352171</pmid><doi>10.1002/chem.201404565</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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source | Wiley |
subjects | Activation alkyl azaarenes Catalysis Catalysts Chemistry iminium catalysis Methodology Michael addition palladium Stereoselectivity Strategy synergistic catalysis |
title | Synergistic Catalysis: Enantioselective Addition of Alkylbenzoxazoles to Enals |
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