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
Hauptverfasser: He, Lin, Lv, Hui, Zhang, Yan-Rong, Ye, Song
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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.
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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). 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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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