Cinchona Alkaloid-Catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones with Trimethylsilyl Trifluoromethane
The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me4NF to afford trifluoromethyl-substituted tertiary pro...
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| Veröffentlicht in: | Organic letters 2010-11, Vol.12 (22), p.5104-5107 |
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| container_end_page | 5107 |
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| container_issue | 22 |
| container_start_page | 5104 |
| container_title | Organic letters |
| container_volume | 12 |
| creator | Kawai, Hiroyuki Tachi, Kentaro Tokunaga, Etsuko Shiro, Motoo Shibata, Norio |
| description | The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me4NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized. |
| doi_str_mv | 10.1021/ol102189c |
| format | Article |
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Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol102189c</identifier><identifier>PMID: 20954725</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkynes - chemistry ; Bromides - chemistry ; Catalysis ; Cinchona Alkaloids - chemistry ; Combinatorial Chemistry Techniques ; Ketones - chemistry ; Methanol - analogs & derivatives ; Methanol - chemical synthesis ; Methanol - chemistry ; Molecular Structure ; Propanols - chemistry ; Quaternary Ammonium Compounds - chemistry ; Stereoisomerism ; Trimethylsilyl Compounds - chemical synthesis ; Trimethylsilyl Compounds - chemistry</subject><ispartof>Organic letters, 2010-11, Vol.12 (22), p.5104-5107</ispartof><rights>Copyright © 2010 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a314t-975622c7e79ccaceb1bd85eadbba54b3baea5ea6e9178de5680e2375fd9a91643</citedby><cites>FETCH-LOGICAL-a314t-975622c7e79ccaceb1bd85eadbba54b3baea5ea6e9178de5680e2375fd9a91643</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/ol102189c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol102189c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20954725$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kawai, Hiroyuki</creatorcontrib><creatorcontrib>Tachi, Kentaro</creatorcontrib><creatorcontrib>Tokunaga, Etsuko</creatorcontrib><creatorcontrib>Shiro, Motoo</creatorcontrib><creatorcontrib>Shibata, Norio</creatorcontrib><title>Cinchona Alkaloid-Catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones with Trimethylsilyl Trifluoromethane</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me4NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized.</description><subject>Alkynes - chemistry</subject><subject>Bromides - chemistry</subject><subject>Catalysis</subject><subject>Cinchona Alkaloids - chemistry</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Ketones - chemistry</subject><subject>Methanol - analogs & derivatives</subject><subject>Methanol - chemical synthesis</subject><subject>Methanol - chemistry</subject><subject>Molecular Structure</subject><subject>Propanols - chemistry</subject><subject>Quaternary Ammonium Compounds - chemistry</subject><subject>Stereoisomerism</subject><subject>Trimethylsilyl Compounds - chemical synthesis</subject><subject>Trimethylsilyl Compounds - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE9LxDAQxYMo7rp68AtILyIeqknaNO1xKf7DBS_ruaTplM2aNmvSIvXTm9J1QfA0M5nfe2QeQpcE3xFMyb3RY0kzeYTmhNEo5JjR40Of4Bk6c26LMfEv2SmaUZyxmFM2Ry5XrdyYVgRL_SG0UVWYi07o4RuqYOmGpoHOKhmsrap1b6zx82bQolOmDUw9qoZ20MErdKYFF3ypbjPCE-aU9rs_WtHCOTqphXZwsa8L9P74sM6fw9Xb00u-XIUiInEXZpwllEoOPJNSSChJWaUMRFWWgsVlVAoQfkwgIzytgCUpBhpxVleZyEgSRwt0M_nurPnswXVFo5wErf0fTO8KnsQsTr3ak7cTKa1xzkJd7PwJwg4FwcWYbXGI2LNXe9e-bKA6kL-ZeuB6AoR0xdb0tvVH_mP0A24-hrM</recordid><startdate>20101119</startdate><enddate>20101119</enddate><creator>Kawai, Hiroyuki</creator><creator>Tachi, Kentaro</creator><creator>Tokunaga, Etsuko</creator><creator>Shiro, Motoo</creator><creator>Shibata, Norio</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>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20101119</creationdate><title>Cinchona Alkaloid-Catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones with Trimethylsilyl Trifluoromethane</title><author>Kawai, Hiroyuki ; Tachi, Kentaro ; Tokunaga, Etsuko ; Shiro, Motoo ; Shibata, Norio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a314t-975622c7e79ccaceb1bd85eadbba54b3baea5ea6e9178de5680e2375fd9a91643</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Alkynes - chemistry</topic><topic>Bromides - chemistry</topic><topic>Catalysis</topic><topic>Cinchona Alkaloids - chemistry</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Ketones - chemistry</topic><topic>Methanol - analogs & derivatives</topic><topic>Methanol - chemical synthesis</topic><topic>Methanol - chemistry</topic><topic>Molecular Structure</topic><topic>Propanols - chemistry</topic><topic>Quaternary Ammonium Compounds - chemistry</topic><topic>Stereoisomerism</topic><topic>Trimethylsilyl Compounds - chemical synthesis</topic><topic>Trimethylsilyl Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kawai, Hiroyuki</creatorcontrib><creatorcontrib>Tachi, Kentaro</creatorcontrib><creatorcontrib>Tokunaga, Etsuko</creatorcontrib><creatorcontrib>Shiro, Motoo</creatorcontrib><creatorcontrib>Shibata, Norio</creatorcontrib><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><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kawai, Hiroyuki</au><au>Tachi, Kentaro</au><au>Tokunaga, Etsuko</au><au>Shiro, Motoo</au><au>Shibata, Norio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cinchona Alkaloid-Catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones with Trimethylsilyl Trifluoromethane</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2010-11-19</date><risdate>2010</risdate><volume>12</volume><issue>22</issue><spage>5104</spage><epage>5107</epage><pages>5104-5107</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me4NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>20954725</pmid><doi>10.1021/ol102189c</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2010-11, Vol.12 (22), p.5104-5107 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_764548917 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkynes - chemistry Bromides - chemistry Catalysis Cinchona Alkaloids - chemistry Combinatorial Chemistry Techniques Ketones - chemistry Methanol - analogs & derivatives Methanol - chemical synthesis Methanol - chemistry Molecular Structure Propanols - chemistry Quaternary Ammonium Compounds - chemistry Stereoisomerism Trimethylsilyl Compounds - chemical synthesis Trimethylsilyl Compounds - chemistry |
| title | Cinchona Alkaloid-Catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones with Trimethylsilyl Trifluoromethane |
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