Silyl Glyoxylates. Conception and Realization of Flexible Conjunctive Reagents for Multicomponent Coupling
This Perspective describes the discovery and development of silyl glyoxylates, a new family of conjunctive reagents for use in multicomponent coupling reactions. The selection of the nucleophilic and electrophilic components determines whether the silyl glyoxylate reagent will function as a syntheti...
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| Veröffentlicht in: | Journal of organic chemistry 2012-05, Vol.77 (10), p.4503-4515 |
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| container_end_page | 4515 |
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| container_issue | 10 |
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| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Boyce, Gregory R Greszler, Stephen N Johnson, Jeffrey S Linghu, Xin Malinowski, Justin T Nicewicz, David A Satterfield, Andrew D Schmitt, Daniel C Steward, Kimberly M |
| description | This Perspective describes the discovery and development of silyl glyoxylates, a new family of conjunctive reagents for use in multicomponent coupling reactions. The selection of the nucleophilic and electrophilic components determines whether the silyl glyoxylate reagent will function as a synthetic equivalent to the dipolar glycolic acid synthon, the glyoxylate anion synthon, or the α-keto ester homoenolate synthon. The ability to select for any of these reaction modes has translated to excellent structural diversity in the derived three- and four-component coupling adducts. Preliminary findings on the development of catalytic reactions using these reagents are detailed, as are the design and discovery of new reactions directed toward particular functional group arrays embedded within bioactive natural products. |
| doi_str_mv | 10.1021/jo300184h |
| format | Article |
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Conception and Realization of Flexible Conjunctive Reagents for Multicomponent Coupling</title><source>ACS Publications</source><source>MEDLINE</source><creator>Boyce, Gregory R ; Greszler, Stephen N ; Johnson, Jeffrey S ; Linghu, Xin ; Malinowski, Justin T ; Nicewicz, David A ; Satterfield, Andrew D ; Schmitt, Daniel C ; Steward, Kimberly M</creator><creatorcontrib>Boyce, Gregory R ; Greszler, Stephen N ; Johnson, Jeffrey S ; Linghu, Xin ; Malinowski, Justin T ; Nicewicz, David A ; Satterfield, Andrew D ; Schmitt, Daniel C ; Steward, Kimberly M</creatorcontrib><description>This Perspective describes the discovery and development of silyl glyoxylates, a new family of conjunctive reagents for use in multicomponent coupling reactions. The selection of the nucleophilic and electrophilic components determines whether the silyl glyoxylate reagent will function as a synthetic equivalent to the dipolar glycolic acid synthon, the glyoxylate anion synthon, or the α-keto ester homoenolate synthon. The ability to select for any of these reaction modes has translated to excellent structural diversity in the derived three- and four-component coupling adducts. Preliminary findings on the development of catalytic reactions using these reagents are detailed, as are the design and discovery of new reactions directed toward particular functional group arrays embedded within bioactive natural products.</description><identifier>ISSN: 0022-3263</identifier><identifier>ISSN: 1520-6904</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo300184h</identifier><identifier>PMID: 22414181</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aliphatic compounds ; Catalysis ; catalytic activity ; chemical reactions ; Chemistry ; Exact sciences and technology ; glycolic acid ; Glyoxylates - chemistry ; Indicators and Reagents - chemistry ; Lewis acids ; Lewis bases ; moieties ; Molecular Structure ; new family ; Organic chemistry ; Organometalloidal and organometallic compounds ; Organosilicon Compounds - chemistry ; Preparations and properties ; Si derivatives ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2012-05, Vol.77 (10), p.4503-4515</ispartof><rights>Copyright © 2012 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a468t-f48a83b3fc36dac89dc5247b61aa64719a72f0981e73bb2a3c82407f44addf6c3</citedby><cites>FETCH-LOGICAL-a468t-f48a83b3fc36dac89dc5247b61aa64719a72f0981e73bb2a3c82407f44addf6c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo300184h$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo300184h$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25912189$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22414181$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Boyce, Gregory R</creatorcontrib><creatorcontrib>Greszler, Stephen N</creatorcontrib><creatorcontrib>Johnson, Jeffrey S</creatorcontrib><creatorcontrib>Linghu, Xin</creatorcontrib><creatorcontrib>Malinowski, Justin T</creatorcontrib><creatorcontrib>Nicewicz, David A</creatorcontrib><creatorcontrib>Satterfield, Andrew D</creatorcontrib><creatorcontrib>Schmitt, Daniel C</creatorcontrib><creatorcontrib>Steward, Kimberly M</creatorcontrib><title>Silyl Glyoxylates. Conception and Realization of Flexible Conjunctive Reagents for Multicomponent Coupling</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>This Perspective describes the discovery and development of silyl glyoxylates, a new family of conjunctive reagents for use in multicomponent coupling reactions. The selection of the nucleophilic and electrophilic components determines whether the silyl glyoxylate reagent will function as a synthetic equivalent to the dipolar glycolic acid synthon, the glyoxylate anion synthon, or the α-keto ester homoenolate synthon. The ability to select for any of these reaction modes has translated to excellent structural diversity in the derived three- and four-component coupling adducts. Preliminary findings on the development of catalytic reactions using these reagents are detailed, as are the design and discovery of new reactions directed toward particular functional group arrays embedded within bioactive natural products.</description><subject>Aliphatic compounds</subject><subject>Catalysis</subject><subject>catalytic activity</subject><subject>chemical reactions</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>glycolic acid</subject><subject>Glyoxylates - chemistry</subject><subject>Indicators and Reagents - chemistry</subject><subject>Lewis acids</subject><subject>Lewis bases</subject><subject>moieties</subject><subject>Molecular Structure</subject><subject>new family</subject><subject>Organic chemistry</subject><subject>Organometalloidal and organometallic compounds</subject><subject>Organosilicon Compounds - chemistry</subject><subject>Preparations and properties</subject><subject>Si derivatives</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0U1rFDEYB_Agil2rB7-AzEXQw7R5m0zmIpTFtkKl4Ms5PJNJtlmyyZjMlK6f3my7bhUEcwlJfvzzJA9Crwk-IZiS03VkGBPJb56gBWkorkWH-VO0wJjSmlHBjtCLnNe4jKZpnqMjSjnhRJIFWn91fuurC7-Nd1sPk8kn1TIGbcbJxVBBGKovBrz7CffraKtzb-5c782OreegJ3drdmZlwpQrG1P1efaT03EzxlD2iptH78LqJXpmwWfzaj8fo-_nH78tL-ur64tPy7OrGriQU225BMl6ZjUTA2jZDbqhvO0FARC8JR201OJOEtOyvqfAtKQct5ZzGAYrNDtGHx5yx7nfmEGXGhJ4NSa3gbRVEZz6-yS4G7WKt4qxRvCGloB3-4AUf8wmT2rjsjbeQzBxzoru_lF2mMr_UoJJgztBCS70_QPVKeacjD1URLDatVEd2ljsmz-fcJC_-1bA2z2ArMHbBEG7_OiajlAiu0cHOpf8OYXy8_-48BfVaLMd</recordid><startdate>20120518</startdate><enddate>20120518</enddate><creator>Boyce, Gregory R</creator><creator>Greszler, Stephen N</creator><creator>Johnson, Jeffrey S</creator><creator>Linghu, Xin</creator><creator>Malinowski, Justin T</creator><creator>Nicewicz, David A</creator><creator>Satterfield, Andrew D</creator><creator>Schmitt, Daniel C</creator><creator>Steward, Kimberly M</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope></search><sort><creationdate>20120518</creationdate><title>Silyl Glyoxylates. Conception and Realization of Flexible Conjunctive Reagents for Multicomponent Coupling</title><author>Boyce, Gregory R ; Greszler, Stephen N ; Johnson, Jeffrey S ; Linghu, Xin ; Malinowski, Justin T ; Nicewicz, David A ; Satterfield, Andrew D ; Schmitt, Daniel C ; Steward, Kimberly M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a468t-f48a83b3fc36dac89dc5247b61aa64719a72f0981e73bb2a3c82407f44addf6c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Aliphatic compounds</topic><topic>Catalysis</topic><topic>catalytic activity</topic><topic>chemical reactions</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>glycolic acid</topic><topic>Glyoxylates - chemistry</topic><topic>Indicators and Reagents - chemistry</topic><topic>Lewis acids</topic><topic>Lewis bases</topic><topic>moieties</topic><topic>Molecular Structure</topic><topic>new family</topic><topic>Organic chemistry</topic><topic>Organometalloidal and organometallic compounds</topic><topic>Organosilicon Compounds - chemistry</topic><topic>Preparations and properties</topic><topic>Si derivatives</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Boyce, Gregory R</creatorcontrib><creatorcontrib>Greszler, Stephen N</creatorcontrib><creatorcontrib>Johnson, Jeffrey S</creatorcontrib><creatorcontrib>Linghu, Xin</creatorcontrib><creatorcontrib>Malinowski, Justin T</creatorcontrib><creatorcontrib>Nicewicz, David A</creatorcontrib><creatorcontrib>Satterfield, Andrew D</creatorcontrib><creatorcontrib>Schmitt, Daniel C</creatorcontrib><creatorcontrib>Steward, Kimberly M</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Boyce, Gregory R</au><au>Greszler, Stephen N</au><au>Johnson, Jeffrey S</au><au>Linghu, Xin</au><au>Malinowski, Justin T</au><au>Nicewicz, David A</au><au>Satterfield, Andrew D</au><au>Schmitt, Daniel C</au><au>Steward, Kimberly M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Silyl Glyoxylates. Conception and Realization of Flexible Conjunctive Reagents for Multicomponent Coupling</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2012-05-18</date><risdate>2012</risdate><volume>77</volume><issue>10</issue><spage>4503</spage><epage>4515</epage><pages>4503-4515</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>This Perspective describes the discovery and development of silyl glyoxylates, a new family of conjunctive reagents for use in multicomponent coupling reactions. The selection of the nucleophilic and electrophilic components determines whether the silyl glyoxylate reagent will function as a synthetic equivalent to the dipolar glycolic acid synthon, the glyoxylate anion synthon, or the α-keto ester homoenolate synthon. 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| source | ACS Publications; MEDLINE |
| subjects | Aliphatic compounds Catalysis catalytic activity chemical reactions Chemistry Exact sciences and technology glycolic acid Glyoxylates - chemistry Indicators and Reagents - chemistry Lewis acids Lewis bases moieties Molecular Structure new family Organic chemistry Organometalloidal and organometallic compounds Organosilicon Compounds - chemistry Preparations and properties Si derivatives Stereoisomerism |
| title | Silyl Glyoxylates. Conception and Realization of Flexible Conjunctive Reagents for Multicomponent Coupling |
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