A Positional Scanning Approach to the Discovery of Dipeptide-Based Catalysts for the Enantioselective Addition of Vinylzinc Reagents to Aldehydes
A combinatorial library of dipeptide N-acylethylenediamine-based ligands was synthesized by parallel solid-phase methods. These ligands were screened in crude form as catalysts for the asymmetric addition of vinylzinc reagents to aldehydes to give chiral allylic alcohols. Three sites of diversity on...
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| Veröffentlicht in: | Journal of organic chemistry 2005-09, Vol.70 (18), p.7408-7417 |
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| container_title | Journal of organic chemistry |
| container_volume | 70 |
| creator | Sprout, Christopher M Richmond, Meaghan L Seto, Christopher T |
| description | A combinatorial library of dipeptide N-acylethylenediamine-based ligands was synthesized by parallel solid-phase methods. These ligands were screened in crude form as catalysts for the asymmetric addition of vinylzinc reagents to aldehydes to give chiral allylic alcohols. Three sites of diversity on the ligands were optimized using a positional scanning approach. The optimized structure from the library, ligand 54, was found to catalyze the formation of 10 different (E)-allylic alcohols with enantioselectivities ranging from 90% to 95% ee. This ligand was effective for both aromatic and α-branched aldehydes, and vinylzinc reagents derived from both bulky and straight chain terminal alkynes. |
| doi_str_mv | 10.1021/jo051342w |
| format | Article |
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These ligands were screened in crude form as catalysts for the asymmetric addition of vinylzinc reagents to aldehydes to give chiral allylic alcohols. Three sites of diversity on the ligands were optimized using a positional scanning approach. The optimized structure from the library, ligand 54, was found to catalyze the formation of 10 different (E)-allylic alcohols with enantioselectivities ranging from 90% to 95% ee. This ligand was effective for both aromatic and α-branched aldehydes, and vinylzinc reagents derived from both bulky and straight chain terminal alkynes.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo051342w</identifier><identifier>PMID: 16122266</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aldehydes - chemistry ; Catalysis ; Catalysts: preparations and properties ; Chemistry ; Combinatorial Chemistry Techniques ; Dipeptides - chemical synthesis ; Exact sciences and technology ; General and physical chemistry ; Ligands ; Organic chemistry ; Organometallic Compounds - chemistry ; Peptides ; Preparations and properties ; Stereoisomerism ; Theory of reactions, general kinetics. Catalysis. 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Org. Chem</addtitle><description>A combinatorial library of dipeptide N-acylethylenediamine-based ligands was synthesized by parallel solid-phase methods. These ligands were screened in crude form as catalysts for the asymmetric addition of vinylzinc reagents to aldehydes to give chiral allylic alcohols. Three sites of diversity on the ligands were optimized using a positional scanning approach. The optimized structure from the library, ligand 54, was found to catalyze the formation of 10 different (E)-allylic alcohols with enantioselectivities ranging from 90% to 95% ee. This ligand was effective for both aromatic and α-branched aldehydes, and vinylzinc reagents derived from both bulky and straight chain terminal alkynes.</description><subject>Aldehydes - chemistry</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Dipeptides - chemical synthesis</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Ligands</subject><subject>Organic chemistry</subject><subject>Organometallic Compounds - chemistry</subject><subject>Peptides</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><subject>Zinc</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc9uEzEQxlcIREPhwAsgX0DisOA_a3v3mIZCkSpRaOBqufZs47Kxt7bTdnkL3hi3iZoLvoys-c03M99U1WuCPxBMycergDlhDb19Us0Ip7gWHW6eVjOMKa0ZFeygepHSFS6Pc_68OiCCUEqFmFV_5-gsJJdd8HpA50Z77_wlmo9jDNqsUA4orwB9csmEG4gTCn35jDBmZ6E-0gksWuishynlhPoQH_Bjr32RTDCAye4G0Nzahx735b-cn4Y_zhv0A_Ql-FJXuswHC6vJQnpZPev1kODVLh5WPz8fLxcn9em3L18X89NaN43M9QXHuumIsA10BKBh0MrOSsaYNa1pWm26ThiLTc_6VgppgPakxWCAd8Bbww6rd1vdsun1BlJW67IkDIP2EDZJiZZT0TasgO-3oIkhpQi9GqNb6zgpgtW9_-rR_8K-2YluLtZg9-TO8AK83QE6GT30UXvj0p6TWJKWysLVW86lDHePeR1_KyGZ5Gp5dq7Ykfx-gpdE8b2uNqnMs4nlnOk_A_4DrKaqkA</recordid><startdate>20050902</startdate><enddate>20050902</enddate><creator>Sprout, Christopher M</creator><creator>Richmond, Meaghan L</creator><creator>Seto, Christopher T</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>20050902</creationdate><title>A Positional Scanning Approach to the Discovery of Dipeptide-Based Catalysts for the Enantioselective Addition of Vinylzinc Reagents to Aldehydes</title><author>Sprout, Christopher M ; Richmond, Meaghan L ; Seto, Christopher T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-b50a4916d4e91ee43e879d7333dc8c48ac996cd0cf3f8767ce2f180ece59e58c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Aldehydes - chemistry</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Dipeptides - chemical synthesis</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Ligands</topic><topic>Organic chemistry</topic><topic>Organometallic Compounds - chemistry</topic><topic>Peptides</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><topic>Zinc</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sprout, Christopher M</creatorcontrib><creatorcontrib>Richmond, Meaghan L</creatorcontrib><creatorcontrib>Seto, Christopher T</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 organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sprout, Christopher M</au><au>Richmond, Meaghan L</au><au>Seto, Christopher T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Positional Scanning Approach to the Discovery of Dipeptide-Based Catalysts for the Enantioselective Addition of Vinylzinc Reagents to Aldehydes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-09-02</date><risdate>2005</risdate><volume>70</volume><issue>18</issue><spage>7408</spage><epage>7417</epage><pages>7408-7417</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A combinatorial library of dipeptide N-acylethylenediamine-based ligands was synthesized by parallel solid-phase methods. These ligands were screened in crude form as catalysts for the asymmetric addition of vinylzinc reagents to aldehydes to give chiral allylic alcohols. Three sites of diversity on the ligands were optimized using a positional scanning approach. The optimized structure from the library, ligand 54, was found to catalyze the formation of 10 different (E)-allylic alcohols with enantioselectivities ranging from 90% to 95% ee. This ligand was effective for both aromatic and α-branched aldehydes, and vinylzinc reagents derived from both bulky and straight chain terminal alkynes.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16122266</pmid><doi>10.1021/jo051342w</doi><tpages>10</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2005-09, Vol.70 (18), p.7408-7417 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Aldehydes - chemistry Catalysis Catalysts: preparations and properties Chemistry Combinatorial Chemistry Techniques Dipeptides - chemical synthesis Exact sciences and technology General and physical chemistry Ligands Organic chemistry Organometallic Compounds - chemistry Peptides Preparations and properties Stereoisomerism Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry Zinc |
| title | A Positional Scanning Approach to the Discovery of Dipeptide-Based Catalysts for the Enantioselective Addition of Vinylzinc Reagents to Aldehydes |
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