N-Vinyl-2-oxazolidinones: Efficient Chiral Dienophiles for the [4 + 2]-Based de Novo Synthesis of New N-2-Deoxyglycosides
Under smooth Eu(fod)3-catalyzed conditions, the inverse-electron demand hetero-Diels−Alder reactions between enantiopure N-vinyl-2-oxazolidinones 1a−f and representative β,γ-unsaturated α-ketoesters proceed with a high degree of endo and facial diastereoselectivity. The elucidation of the stereostru...
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| Veröffentlicht in: | Journal of organic chemistry 2004-06, Vol.69 (12), p.4192-4202 |
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| container_title | Journal of organic chemistry |
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| creator | Gaulon, Catherine Dhal, Robert Chapin, Teddy Maisonneuve, Vincent Dujardin, Gilles |
| description | Under smooth Eu(fod)3-catalyzed conditions, the inverse-electron demand hetero-Diels−Alder reactions between enantiopure N-vinyl-2-oxazolidinones 1a−f and representative β,γ-unsaturated α-ketoesters proceed with a high degree of endo and facial diastereoselectivity. The elucidation of the stereostructure of these adducts, performed by X-ray analysis or chemical correlation, shows that the endo-selective cycloaddition process is facially controlled in favor of the (2S,4S)-adduct when starting from a (4S)-dienophile or vice versa. The specific interest of the adducts 10a−e, derived from (E)-4-tert-butoxymethylene pyruvic acid methyl ester 9, has been exemplified by the two-step and highly stereoselective transformation of these adducts into the new and valuable N-2-deoxyglycosyl-oxazolidinones 12a−e, isolated in a pure diastereo- and enantiomeric form. |
| doi_str_mv | 10.1021/jo040102y |
| format | Article |
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The elucidation of the stereostructure of these adducts, performed by X-ray analysis or chemical correlation, shows that the endo-selective cycloaddition process is facially controlled in favor of the (2S,4S)-adduct when starting from a (4S)-dienophile or vice versa. The specific interest of the adducts 10a−e, derived from (E)-4-tert-butoxymethylene pyruvic acid methyl ester 9, has been exemplified by the two-step and highly stereoselective transformation of these adducts into the new and valuable N-2-deoxyglycosyl-oxazolidinones 12a−e, isolated in a pure diastereo- and enantiomeric form.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo040102y</identifier><identifier>PMID: 15176848</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Carbohydrates with 4, 5, 6, ... 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Org. Chem</addtitle><description>Under smooth Eu(fod)3-catalyzed conditions, the inverse-electron demand hetero-Diels−Alder reactions between enantiopure N-vinyl-2-oxazolidinones 1a−f and representative β,γ-unsaturated α-ketoesters proceed with a high degree of endo and facial diastereoselectivity. The elucidation of the stereostructure of these adducts, performed by X-ray analysis or chemical correlation, shows that the endo-selective cycloaddition process is facially controlled in favor of the (2S,4S)-adduct when starting from a (4S)-dienophile or vice versa. The specific interest of the adducts 10a−e, derived from (E)-4-tert-butoxymethylene pyruvic acid methyl ester 9, has been exemplified by the two-step and highly stereoselective transformation of these adducts into the new and valuable N-2-deoxyglycosyl-oxazolidinones 12a−e, isolated in a pure diastereo- and enantiomeric form.</description><subject>Carbohydrates with 4, 5, 6, ... 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Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gaulon, Catherine</creatorcontrib><creatorcontrib>Dhal, Robert</creatorcontrib><creatorcontrib>Chapin, Teddy</creatorcontrib><creatorcontrib>Maisonneuve, Vincent</creatorcontrib><creatorcontrib>Dujardin, Gilles</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</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>Gaulon, Catherine</au><au>Dhal, Robert</au><au>Chapin, Teddy</au><au>Maisonneuve, Vincent</au><au>Dujardin, Gilles</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N-Vinyl-2-oxazolidinones: Efficient Chiral Dienophiles for the [4 + 2]-Based de Novo Synthesis of New N-2-Deoxyglycosides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2004-06-11</date><risdate>2004</risdate><volume>69</volume><issue>12</issue><spage>4192</spage><epage>4202</epage><pages>4192-4202</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Under smooth Eu(fod)3-catalyzed conditions, the inverse-electron demand hetero-Diels−Alder reactions between enantiopure N-vinyl-2-oxazolidinones 1a−f and representative β,γ-unsaturated α-ketoesters proceed with a high degree of endo and facial diastereoselectivity. The elucidation of the stereostructure of these adducts, performed by X-ray analysis or chemical correlation, shows that the endo-selective cycloaddition process is facially controlled in favor of the (2S,4S)-adduct when starting from a (4S)-dienophile or vice versa. 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| subjects | Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Organic chemistry Preparations and properties |
| title | N-Vinyl-2-oxazolidinones: Efficient Chiral Dienophiles for the [4 + 2]-Based de Novo Synthesis of New N-2-Deoxyglycosides |
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