Catalyzed Asymmetric Aryl Transfer Reactions to Aldehydes with Boronic Acids as Aryl Source
Chiral diaryl methanols are important intermediates for the synthesis of biologically active compounds. Here, we describe a flexible method for their catalyzed asymmetric synthesis from readily available starting materials. Noteworthy is the fact that with a single catalyst both enantiomers of the p...
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| Veröffentlicht in: | Journal of the American Chemical Society 2002-12, Vol.124 (50), p.14850-14851 |
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| container_end_page | 14851 |
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| container_issue | 50 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 124 |
| creator | Bolm, Carsten Rudolph, Jens |
| description | Chiral diaryl methanols are important intermediates for the synthesis of biologically active compounds. Here, we describe a flexible method for their catalyzed asymmetric synthesis from readily available starting materials. Noteworthy is the fact that with a single catalyst both enantiomers of the product are accessible simply by choosing the appropriate combination of aryl boronic acid or aldehyde as aryl donor and acceptor, respectively. The catalysis with a planar-chiral ferrocene is easy to perform and yields a broad range of products with excellent enantioselectivities (up to 98% ee). |
| doi_str_mv | 10.1021/ja028518l |
| format | Article |
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Am. Chem. Soc</addtitle><description>Chiral diaryl methanols are important intermediates for the synthesis of biologically active compounds. Here, we describe a flexible method for their catalyzed asymmetric synthesis from readily available starting materials. Noteworthy is the fact that with a single catalyst both enantiomers of the product are accessible simply by choosing the appropriate combination of aryl boronic acid or aldehyde as aryl donor and acceptor, respectively. The catalysis with a planar-chiral ferrocene is easy to perform and yields a broad range of products with excellent enantioselectivities (up to 98% ee).</description><subject>Aldehydes - chemistry</subject><subject>Benzyl Alcohols - chemical synthesis</subject><subject>Boronic Acids - chemistry</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Methanol - analogs & derivatives</subject><subject>Methanol - chemistry</subject><subject>Organic chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1vEzEQhi0EoqFw4A8gX0DqYant9a69xzSUDylqURMucLAm9qy6YT9az0aw_fW4StRcOI1G87yvRg9jb6X4KIWS51sQyhbSts_YTBZKZIVU5XM2E0KozNgyP2GviLZp1crKl-xEKm2KXNoZ-7WAEdrpAQOf09R1OMbG83mcWr6O0FONkd8g-LEZeuLjwOdtwNspIPE_zXjLL4Y49I8J3wTiQPvoathFj6_ZixpawjeHecp-fL5cL75my-sv3xbzZQa5qcZMbaw2JVoIYAMIRG1DoYUyAqDMS9C1BQ0WhQnGy0rXuJEJqAqpdcAq5Kfsw773Lg73O6TRdQ15bFvocdiRM8oYqXOVwLM96ONAFLF2d7HpIE5OCvdo0j2ZTOy7Q-lu02E4kgd1CXh_AIA8tHWy5Rs6ctqmD6sycdmea2jEv093iL9daXJTuPX3lfv5qVyu9MWNuzr2gie3TSL75O4_D_4D8MWWWA</recordid><startdate>20021218</startdate><enddate>20021218</enddate><creator>Bolm, Carsten</creator><creator>Rudolph, Jens</creator><general>American Chemical Society</general><scope>BSCLL</scope><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></search><sort><creationdate>20021218</creationdate><title>Catalyzed Asymmetric Aryl Transfer Reactions to Aldehydes with Boronic Acids as Aryl Source</title><author>Bolm, Carsten ; Rudolph, Jens</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-2b8476e8ada8da0ee48d540270aa636a4f8a4a8e07d7c194feb1d5495144de9d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Aldehydes - chemistry</topic><topic>Benzyl Alcohols - chemical synthesis</topic><topic>Boronic Acids - chemistry</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Methanol - analogs & derivatives</topic><topic>Methanol - chemistry</topic><topic>Organic chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bolm, Carsten</creatorcontrib><creatorcontrib>Rudolph, Jens</creatorcontrib><collection>Istex</collection><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><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bolm, Carsten</au><au>Rudolph, Jens</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalyzed Asymmetric Aryl Transfer Reactions to Aldehydes with Boronic Acids as Aryl Source</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2002-12-18</date><risdate>2002</risdate><volume>124</volume><issue>50</issue><spage>14850</spage><epage>14851</epage><pages>14850-14851</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>Chiral diaryl methanols are important intermediates for the synthesis of biologically active compounds. Here, we describe a flexible method for their catalyzed asymmetric synthesis from readily available starting materials. Noteworthy is the fact that with a single catalyst both enantiomers of the product are accessible simply by choosing the appropriate combination of aryl boronic acid or aldehyde as aryl donor and acceptor, respectively. 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| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2002-12, Vol.124 (50), p.14850-14851 |
| issn | 0002-7863 1520-5126 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Aldehydes - chemistry Benzyl Alcohols - chemical synthesis Boronic Acids - chemistry Catalysis Chemistry Exact sciences and technology Methanol - analogs & derivatives Methanol - chemistry Organic chemistry |
| title | Catalyzed Asymmetric Aryl Transfer Reactions to Aldehydes with Boronic Acids as Aryl Source |
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