Formal Cycloaddition of Disubstituted Ketenes with 2-Oxoaldehydes Catalyzed by Chiral N-Heterocyclic Carbenes
Chiral N-hetereocyclic carbenes were found to be efficient catalysts for the formal [2 + 2] cycloaddition reactions of alkyl(aryl)ketenes with 2-oxoaldehydes to afford β-lactones with α-quaternary-β-tertiary stereocenters in high yields with good diastereoselectivities and excellent enantioselectivi...
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Veröffentlicht in: | Journal of organic chemistry 2008-10, Vol.73 (20), p.8101-8103 |
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container_title | Journal of organic chemistry |
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creator | He, Lin Lv, Hui Zhang, Yan-Rong Ye, Song |
description | Chiral N-hetereocyclic carbenes were found to be efficient catalysts for the formal [2 + 2] cycloaddition reactions of alkyl(aryl)ketenes with 2-oxoaldehydes to afford β-lactones with α-quaternary-β-tertiary stereocenters in high yields with good diastereoselectivities and excellent enantioselectivities (up to 99% ee). Both alkyl(aryl)ketenes and diarylketene worked well in this reaction. |
doi_str_mv | 10.1021/jo801494f |
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Both alkyl(aryl)ketenes and diarylketene worked well in this reaction.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo801494f</identifier><identifier>PMID: 18816140</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aldehydes - chemistry ; Catalysis ; Catalysts: preparations and properties ; Chemistry ; Ethylenes - chemistry ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Ketones - chemistry ; Methane - analogs & derivatives ; Methane - chemistry ; Organic chemistry ; Preparations and properties ; Stereoisomerism ; Theory of reactions, general kinetics. Catalysis. 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Org. Chem</addtitle><description>Chiral N-hetereocyclic carbenes were found to be efficient catalysts for the formal [2 + 2] cycloaddition reactions of alkyl(aryl)ketenes with 2-oxoaldehydes to afford β-lactones with α-quaternary-β-tertiary stereocenters in high yields with good diastereoselectivities and excellent enantioselectivities (up to 99% ee). Both alkyl(aryl)ketenes and diarylketene worked well in this reaction.</description><subject>Aldehydes - chemistry</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Ethylenes - chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Ketones - chemistry</subject><subject>Methane - analogs & derivatives</subject><subject>Methane - chemistry</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0Mtu1DAUBmALgehQWPACKBuQWITaTnzJEoVeUAsFMRR21ontaFySuLUd0fD0uJrRdFNvLNnf-XX0I_Sa4A8EU3J07SUmdVP3T9CKMIpL3uD6KVphTGlZUV4doBcxXuN8GGPP0QGRknBS4xUaT3wYYSjaRQ8ejHHJ-anwffHJxbmLyaU5WVOc22QnG4u_Lm0KWl7eeRiM3Swmv7WQYFj-ZdUtRbtxIcd9Lc_yRPA6xzqdSeju51-iZz0M0b7a3Yfo58nxuj0rLy5PP7cfL0qoJEmlMNBxAtJq3BhGhdDGcE07YyXXWIAEgW3FAEtca95XwDVjWOYJ0wtS19UherfNvQn-drYxqdFFbYcBJuvnqHjDa9E0IsP3W6iDjzHYXt0EN0JYFMHqvlu17zbbN7vQuRuteZC7MjN4uwMQNQx9gEm7uHcUC8EYqbIrt87FZO_2_xD-KC4qwdT62w_16_v6y-nV-W919ZALOuZ95jDl7h5Z8D8qcZ2y</recordid><startdate>20081017</startdate><enddate>20081017</enddate><creator>He, Lin</creator><creator>Lv, Hui</creator><creator>Zhang, Yan-Rong</creator><creator>Ye, Song</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>20081017</creationdate><title>Formal Cycloaddition of Disubstituted Ketenes with 2-Oxoaldehydes Catalyzed by Chiral N-Heterocyclic Carbenes</title><author>He, Lin ; Lv, Hui ; Zhang, Yan-Rong ; Ye, Song</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-7dab61a8ec09d5277cdd6c2bde86c07a8a70e35a0804c6f3a6c55081a8df71443</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Aldehydes - chemistry</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Ethylenes - chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Ketones - chemistry</topic><topic>Methane - analogs & derivatives</topic><topic>Methane - chemistry</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>He, Lin</creatorcontrib><creatorcontrib>Lv, Hui</creatorcontrib><creatorcontrib>Zhang, Yan-Rong</creatorcontrib><creatorcontrib>Ye, Song</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>He, Lin</au><au>Lv, Hui</au><au>Zhang, Yan-Rong</au><au>Ye, Song</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Formal Cycloaddition of Disubstituted Ketenes with 2-Oxoaldehydes Catalyzed by Chiral N-Heterocyclic Carbenes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2008-10-17</date><risdate>2008</risdate><volume>73</volume><issue>20</issue><spage>8101</spage><epage>8103</epage><pages>8101-8103</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Chiral N-hetereocyclic carbenes were found to be efficient catalysts for the formal [2 + 2] cycloaddition reactions of alkyl(aryl)ketenes with 2-oxoaldehydes to afford β-lactones with α-quaternary-β-tertiary stereocenters in high yields with good diastereoselectivities and excellent enantioselectivities (up to 99% ee). Both alkyl(aryl)ketenes and diarylketene worked well in this reaction.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18816140</pmid><doi>10.1021/jo801494f</doi><tpages>3</tpages></addata></record> |
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subjects | Aldehydes - chemistry Catalysis Catalysts: preparations and properties Chemistry Ethylenes - chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Ketones - chemistry Methane - analogs & derivatives Methane - chemistry Organic chemistry Preparations and properties Stereoisomerism Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
title | Formal Cycloaddition of Disubstituted Ketenes with 2-Oxoaldehydes Catalyzed by Chiral N-Heterocyclic Carbenes |
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