Picolinoxy Group, a New Leaving Group for anti SN2′ Selective Allylic Substitution with Aryl Anions Based on Grignard Reagents
The picolinoxy group was found to be an extremely powerful leaving group for allylic substitution with aryl nucleophiles derived from ArMgBr and CuBr•Me2S. The substitution proceeds with anti SN2′ pathway and with high chirality transfer. The electron-withdrawing effect of the pyridyl group and chel...
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| Veröffentlicht in: | Organic letters 2008-05, Vol.10 (9), p.1719-1722 |
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| container_end_page | 1722 |
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| container_issue | 9 |
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| container_title | Organic letters |
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| creator | Kiyotsuka, Yohei Acharya, Hukum P Katayama, Yuji Hyodo, Tomonori Kobayashi, Yuichi |
| description | The picolinoxy group was found to be an extremely powerful leaving group for allylic substitution with aryl nucleophiles derived from ArMgBr and CuBr•Me2S. The substitution proceeds with anti SN2′ pathway and with high chirality transfer. The electron-withdrawing effect of the pyridyl group and chelation to MgBr2 are likely the origin of success. Results suggesting these effects were obtained. |
| doi_str_mv | 10.1021/ol800300x |
| format | Article |
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The substitution proceeds with anti SN2′ pathway and with high chirality transfer. The electron-withdrawing effect of the pyridyl group and chelation to MgBr2 are likely the origin of success. 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Lett</addtitle><description>The picolinoxy group was found to be an extremely powerful leaving group for allylic substitution with aryl nucleophiles derived from ArMgBr and CuBr•Me2S. The substitution proceeds with anti SN2′ pathway and with high chirality transfer. The electron-withdrawing effect of the pyridyl group and chelation to MgBr2 are likely the origin of success. Results suggesting these effects were obtained.</description><subject>Allyl Compounds - chemical synthesis</subject><subject>Allyl Compounds - chemistry</subject><subject>Anions</subject><subject>Indicators and Reagents - chemical synthesis</subject><subject>Indicators and Reagents - chemistry</subject><subject>Molecular Structure</subject><subject>Picolinic Acids - chemistry</subject><subject>Piperidines - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9UU1PAjEQbYxG8OPgHzC96Em0H7ulPSJRNCFoRM-bbilYUlpsu8Le_E3-JH-JS1DmMjNvXibz5gFwhtE1RgTfeMsRogit90Ab54R2uign-7uaoRY4inGOEG4QcQhamFPBOM_b4OvZKG-N8-saDoKvlldQwpFewaGWn8bNtiCc-gClSwaOR-Tn6xuOtdUqmU8Ne9bW1ig4rsqYTKqS8Q6uTHqHvVBb2HNNH-GtjHoCm8kgmJmTYQJftJxpl-IJOJhKG_XpXz4Gb_d3r_2HzvBp8NjvDTsS51nqZF1OFKGUECmmnJWKIcF1I4eQTDLCNpFxNBEK8aykQgnEdd4ILjOWZwzRY3C53bsM_qPSMRULE5W2Vjrtq1gwgWmXC9IQz_-IVbnQk2IZzEKGuvj_WUO42BKkisXcV8E1dxcYFRsvip0X9Bfs4Xip</recordid><startdate>20080501</startdate><enddate>20080501</enddate><creator>Kiyotsuka, Yohei</creator><creator>Acharya, Hukum P</creator><creator>Katayama, Yuji</creator><creator>Hyodo, Tomonori</creator><creator>Kobayashi, Yuichi</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20080501</creationdate><title>Picolinoxy Group, a New Leaving Group for anti SN2′ Selective Allylic Substitution with Aryl Anions Based on Grignard Reagents</title><author>Kiyotsuka, Yohei ; Acharya, Hukum P ; Katayama, Yuji ; Hyodo, Tomonori ; Kobayashi, Yuichi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a154t-4782c23322a9f86bc6098e152224a6266666480d9c084b39c908e5011b4654603</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Allyl Compounds - chemical synthesis</topic><topic>Allyl Compounds - chemistry</topic><topic>Anions</topic><topic>Indicators and Reagents - chemical synthesis</topic><topic>Indicators and Reagents - chemistry</topic><topic>Molecular Structure</topic><topic>Picolinic Acids - chemistry</topic><topic>Piperidines - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kiyotsuka, Yohei</creatorcontrib><creatorcontrib>Acharya, Hukum P</creatorcontrib><creatorcontrib>Katayama, Yuji</creatorcontrib><creatorcontrib>Hyodo, Tomonori</creatorcontrib><creatorcontrib>Kobayashi, Yuichi</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kiyotsuka, Yohei</au><au>Acharya, Hukum P</au><au>Katayama, Yuji</au><au>Hyodo, Tomonori</au><au>Kobayashi, Yuichi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Picolinoxy Group, a New Leaving Group for anti SN2′ Selective Allylic Substitution with Aryl Anions Based on Grignard Reagents</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| ispartof | Organic letters, 2008-05, Vol.10 (9), p.1719-1722 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Allyl Compounds - chemical synthesis Allyl Compounds - chemistry Anions Indicators and Reagents - chemical synthesis Indicators and Reagents - chemistry Molecular Structure Picolinic Acids - chemistry Piperidines - chemistry Stereoisomerism |
| title | Picolinoxy Group, a New Leaving Group for anti SN2′ Selective Allylic Substitution with Aryl Anions Based on Grignard Reagents |
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