Lipase-Mediated Resolution of 4-TMS-3-butyn-2-ol and Use of the Mesylate Derivatives as a Precursor to a Highly Stereoselective Chiral Allenylindium Reagent
An improved procedure for the resolution of 4-trimethylsilyl-3-butyn-2-ol has been developed. The mesylate derivatives of the resolved alcohols have been found to undergo highly enantio-, regio-, and diastereoselective additions to aldehydes, leading to homopropargylic alcohol adducts.
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| Veröffentlicht in: | Organic letters 2001-10, Vol.3 (21), p.3369-3372 |
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| container_title | Organic letters |
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| creator | Marshall, James A Chobanian, Harry R Yanik, Mathew M |
| description | An improved procedure for the resolution of 4-trimethylsilyl-3-butyn-2-ol has been developed. The mesylate derivatives of the resolved alcohols have been found to undergo highly enantio-, regio-, and diastereoselective additions to aldehydes, leading to homopropargylic alcohol adducts. |
| doi_str_mv | 10.1021/ol016605x |
| format | Article |
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The mesylate derivatives of the resolved alcohols have been found to undergo highly enantio-, regio-, and diastereoselective additions to aldehydes, leading to homopropargylic alcohol adducts.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol016605x</identifier><identifier>PMID: 11594836</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Acetylation ; Alkynes - chemistry ; Butanols - chemistry ; Chromatography, Liquid - methods ; Indicators and Reagents ; Lipase - metabolism ; Lipase - pharmacology ; Mesylates - chemistry ; Methods ; Propanols - chemistry ; Stereoisomerism ; Trimethylsilyl Compounds - chemistry</subject><ispartof>Organic letters, 2001-10, Vol.3 (21), p.3369-3372</ispartof><rights>Copyright © 2001 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a377t-7d3cd67bb7bde0cc2ed6cc4d4b5ede39cfdb129108a8d45aff2baa88bf43c703</citedby><cites>FETCH-LOGICAL-a377t-7d3cd67bb7bde0cc2ed6cc4d4b5ede39cfdb129108a8d45aff2baa88bf43c703</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/ol016605x$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol016605x$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11594836$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Marshall, James A</creatorcontrib><creatorcontrib>Chobanian, Harry R</creatorcontrib><creatorcontrib>Yanik, Mathew M</creatorcontrib><title>Lipase-Mediated Resolution of 4-TMS-3-butyn-2-ol and Use of the Mesylate Derivatives as a Precursor to a Highly Stereoselective Chiral Allenylindium Reagent</title><title>Organic letters</title><addtitle>Org. 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The mesylate derivatives of the resolved alcohols have been found to undergo highly enantio-, regio-, and diastereoselective additions to aldehydes, leading to homopropargylic alcohol adducts.</description><subject>Acetylation</subject><subject>Alkynes - chemistry</subject><subject>Butanols - chemistry</subject><subject>Chromatography, Liquid - methods</subject><subject>Indicators and Reagents</subject><subject>Lipase - metabolism</subject><subject>Lipase - pharmacology</subject><subject>Mesylates - chemistry</subject><subject>Methods</subject><subject>Propanols - chemistry</subject><subject>Stereoisomerism</subject><subject>Trimethylsilyl Compounds - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkUtrGzEQx0VJqBO3h36BoksCOSiVVvs8GucJNi2Ne170mI1l5JUraUP2u_TDRsYmuRQGZkbzmz-jGYS-MXrNaMZ-OEtZWdLi9RM6Y0XGSUWL7OQ9LukEnYewoZSll-YzmiTf5DUvz9C_hdmJAGQJ2ogIGv-G4OwQjeux63BOVssnwokc4tiTjDiLRa_xnwD7alwDXkIYberEN-DNi4jmBQIWyfAvD2rwwXkcXUofzPPajvgpggcXwILas3i-Nl5YPLMW-tGaXpthm4YQz9DHL-i0EzbA16OfotXd7Wr-QBY_7x_nswURvKoiqTRXuqykrKQGqlQGulQq17ksQANvVKclyxpGa1HrvBBdl0kh6lp2OVcV5VN0eZDdefd3gBDbrQkKrBU9uCG0VcYaymuWwKsDqLwLwUPX7rzZCj-2jLb7S7Tvl0js96PoILegP8jj6hNwcQCECu3GDb5PX_yP0Bv0pJK9</recordid><startdate>20011018</startdate><enddate>20011018</enddate><creator>Marshall, James A</creator><creator>Chobanian, Harry R</creator><creator>Yanik, Mathew M</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>20011018</creationdate><title>Lipase-Mediated Resolution of 4-TMS-3-butyn-2-ol and Use of the Mesylate Derivatives as a Precursor to a Highly Stereoselective Chiral Allenylindium Reagent</title><author>Marshall, James A ; Chobanian, Harry R ; Yanik, Mathew M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a377t-7d3cd67bb7bde0cc2ed6cc4d4b5ede39cfdb129108a8d45aff2baa88bf43c703</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Acetylation</topic><topic>Alkynes - chemistry</topic><topic>Butanols - chemistry</topic><topic>Chromatography, Liquid - methods</topic><topic>Indicators and Reagents</topic><topic>Lipase - metabolism</topic><topic>Lipase - pharmacology</topic><topic>Mesylates - chemistry</topic><topic>Methods</topic><topic>Propanols - chemistry</topic><topic>Stereoisomerism</topic><topic>Trimethylsilyl Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Marshall, James A</creatorcontrib><creatorcontrib>Chobanian, Harry R</creatorcontrib><creatorcontrib>Yanik, Mathew M</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>Marshall, James A</au><au>Chobanian, Harry R</au><au>Yanik, Mathew M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lipase-Mediated Resolution of 4-TMS-3-butyn-2-ol and Use of the Mesylate Derivatives as a Precursor to a Highly Stereoselective Chiral Allenylindium Reagent</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2001-10-18</date><risdate>2001</risdate><volume>3</volume><issue>21</issue><spage>3369</spage><epage>3372</epage><pages>3369-3372</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>An improved procedure for the resolution of 4-trimethylsilyl-3-butyn-2-ol has been developed. The mesylate derivatives of the resolved alcohols have been found to undergo highly enantio-, regio-, and diastereoselective additions to aldehydes, leading to homopropargylic alcohol adducts.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11594836</pmid><doi>10.1021/ol016605x</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2001-10, Vol.3 (21), p.3369-3372 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_72190381 |
| source | ACS Publications; MEDLINE |
| subjects | Acetylation Alkynes - chemistry Butanols - chemistry Chromatography, Liquid - methods Indicators and Reagents Lipase - metabolism Lipase - pharmacology Mesylates - chemistry Methods Propanols - chemistry Stereoisomerism Trimethylsilyl Compounds - chemistry |
| title | Lipase-Mediated Resolution of 4-TMS-3-butyn-2-ol and Use of the Mesylate Derivatives as a Precursor to a Highly Stereoselective Chiral Allenylindium Reagent |
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