IndiumV3, Main, Repository, bibRecord, 001420

Synthesis of Sugar-Derived 2-Nitroalkanols via Henry Reaction Promoted by Samarium Diiodide or Indium

Identifieur interne : 001420 ( Main/Repository ); précédent : 001419; suivant : 001421

Synthesis of Sugar-Derived 2-Nitroalkanols via Henry Reaction Promoted by Samarium Diiodide or Indium

Auteurs : RBID : Pascal:12-0414333

Descripteurs français

Pascal (Inist)
- Synthèse chimique, Oside, Samarium II Iodure, Indium, Composé nitro, Aldéhyde, Métal, Diastéréoisomère, Effet stérique, Encombrement stérique, Aldolisation, Lanthanide Composé, Réaction de Henry, Réaction Henry.
Wicri :
- concept : Métal.

English descriptors

KwdEn :
- Aldehyde, Aldol condensation, Chemical synthesis, Diastereomer, Henry reaction, Indium, Lanthanide Compounds, Metal, Nitro compound, Oside, Samarium II Iodides, Steric effect, Steric hindrance.

Abstract

We present herein an improved synthesis of nitro sugars, consisting of a Henry-type reaction of bromonitromethane and sugar aldehydes. The reaction can be promoted by either SmI₂ or indium metal, yielding in both cases high yields and good diastereoisomeric ratios. However, while the SmI₂-promoted reaction is very sensitive to steric factors and only gives satisfactory results with bromonitromethane, the indium-mediated reaction is not subjected to this limitation, giving excellent results with bromonitromethane as well as more hindered bromonitroalkanes.

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Pascal:12-0414333

Le document en format XML

<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en" level="a">Synthesis of Sugar-Derived 2-Nitroalkanols via Henry Reaction Promoted by Samarium Diiodide or Indium</title>
<author><name sortKey="Rodriguez Solla, Humberto" uniqKey="Rodriguez Solla H">Humberto Rodriguez-Solla</name>
<affiliation wicri:level="2"><inist:fA14 i1="01"><s1>Departamento Quimica Organica e Inorganica, Universidad de Oviedo, C/ Julian Claveria 8</s1>
<s2>33006 Oviedo</s2>
<s3>ESP</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
</inist:fA14>
<country>Espagne</country>
<placeName><region nuts="2" type="communauté">Principauté des Asturies</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Alvaredo, Noemi" uniqKey="Alvaredo N">Noemi Alvaredo</name>
<affiliation wicri:level="2"><inist:fA14 i1="01"><s1>Departamento Quimica Organica e Inorganica, Universidad de Oviedo, C/ Julian Claveria 8</s1>
<s2>33006 Oviedo</s2>
<s3>ESP</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
</inist:fA14>
<country>Espagne</country>
<placeName><region nuts="2" type="communauté">Principauté des Asturies</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Soengas, Raquel G" uniqKey="Soengas R">Raquel G. Soengas</name>
<affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Department of Chemistry & QOPNA, University of Aveiro</s1>
<s2>3810-193 Aveiro</s2>
<s3>PRT</s3>
<sZ>3 aut.</sZ>
</inist:fA14>
<country>Portugal</country>
<wicri:noRegion>3810-193 Aveiro</wicri:noRegion>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="inist">12-0414333</idno>
<date when="2012">2012</date>
<idno type="stanalyst">PASCAL 12-0414333 INIST</idno>
<idno type="RBID">Pascal:12-0414333</idno>
<idno type="wicri:Area/Main/Corpus">001689</idno>
<idno type="wicri:Area/Main/Repository">001420</idno>
</publicationStmt>
<seriesStmt><idno type="ISSN">0936-5214</idno>
<title level="j" type="abbreviated">Synlett : (Stuttg.)</title>
<title level="j" type="main">Synlett : (Stuttgart)</title>
</seriesStmt>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aldehyde</term>
<term>Aldol condensation</term>
<term>Chemical synthesis</term>
<term>Diastereomer</term>
<term>Henry reaction</term>
<term>Indium</term>
<term>Lanthanide Compounds</term>
<term>Metal</term>
<term>Nitro compound</term>
<term>Oside</term>
<term>Samarium II Iodides</term>
<term>Steric effect</term>
<term>Steric hindrance</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Synthèse chimique</term>
<term>Oside</term>
<term>Samarium II Iodure</term>
<term>Indium</term>
<term>Composé nitro</term>
<term>Aldéhyde</term>
<term>Métal</term>
<term>Diastéréoisomère</term>
<term>Effet stérique</term>
<term>Encombrement stérique</term>
<term>Aldolisation</term>
<term>Lanthanide Composé</term>
<term>Réaction de Henry</term>
<term>Réaction Henry</term>
</keywords>
<keywords scheme="Wicri" type="concept" xml:lang="fr"><term>Métal</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">We present herein an improved synthesis of nitro sugars, consisting of a Henry-type reaction of bromonitromethane and sugar aldehydes. The reaction can be promoted by either SmI<sub>2</sub>
 or indium metal, yielding in both cases high yields and good diastereoisomeric ratios. However, while the SmI<sub>2</sub>
-promoted reaction is very sensitive to steric factors and only gives satisfactory results with bromonitromethane, the indium-mediated reaction is not subjected to this limitation, giving excellent results with bromonitromethane as well as more hindered bromonitroalkanes.</div>
</front>
</TEI>
<inist><standard h6="B"><pA><fA01 i1="01" i2="1"><s0>0936-5214</s0>
</fA01>
<fA03 i2="1"><s0>Synlett : (Stuttg.)</s0>
</fA03>
<fA06><s2>14</s2>
</fA06>
<fA08 i1="01" i2="1" l="ENG"><s1>Synthesis of Sugar-Derived 2-Nitroalkanols via Henry Reaction Promoted by Samarium Diiodide or Indium</s1>
</fA08>
<fA11 i1="01" i2="1"><s1>RODRIGUEZ-SOLLA (Humberto)</s1>
</fA11>
<fA11 i1="02" i2="1"><s1>ALVAREDO (Noemi)</s1>
</fA11>
<fA11 i1="03" i2="1"><s1>SOENGAS (Raquel G.)</s1>
</fA11>
<fA14 i1="01"><s1>Departamento Quimica Organica e Inorganica, Universidad de Oviedo, C/ Julian Claveria 8</s1>
<s2>33006 Oviedo</s2>
<s3>ESP</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
</fA14>
<fA14 i1="02"><s1>Department of Chemistry & QOPNA, University of Aveiro</s1>
<s2>3810-193 Aveiro</s2>
<s3>PRT</s3>
<sZ>3 aut.</sZ>
</fA14>
<fA20><s1>2083-2086</s1>
</fA20>
<fA21><s1>2012</s1>
</fA21>
<fA23 i1="01"><s0>ENG</s0>
</fA23>
<fA43 i1="01"><s1>INIST</s1>
<s2>22428</s2>
<s5>354000508118020110</s5>
</fA43>
<fA44><s0>0000</s0>
<s1>© 2012 INIST-CNRS. All rights reserved.</s1>
</fA44>
<fA45><s0>22 ref.</s0>
</fA45>
<fA47 i1="01" i2="1"><s0>12-0414333</s0>
</fA47>
<fA60><s1>P</s1>
<s3>CR</s3>
</fA60>
<fA61><s0>A</s0>
</fA61>
<fA64 i1="01" i2="1"><s0>Synlett : (Stuttgart)</s0>
</fA64>
<fA66 i1="01"><s0>DEU</s0>
</fA66>
<fC01 i1="01" l="ENG"><s0>We present herein an improved synthesis of nitro sugars, consisting of a Henry-type reaction of bromonitromethane and sugar aldehydes. The reaction can be promoted by either SmI<sub>2</sub>
 or indium metal, yielding in both cases high yields and good diastereoisomeric ratios. However, while the SmI<sub>2</sub>
-promoted reaction is very sensitive to steric factors and only gives satisfactory results with bromonitromethane, the indium-mediated reaction is not subjected to this limitation, giving excellent results with bromonitromethane as well as more hindered bromonitroalkanes.</s0>
</fC01>
<fC02 i1="01" i2="X"><s0>001C03C07A</s0>
</fC02>
<fC03 i1="01" i2="X" l="FRE"><s0>Synthèse chimique</s0>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="ENG"><s0>Chemical synthesis</s0>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="SPA"><s0>Síntesis química</s0>
<s5>01</s5>
</fC03>
<fC03 i1="02" i2="X" l="FRE"><s0>Oside</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="ENG"><s0>Oside</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="SPA"><s0>Osido</s0>
<s5>02</s5>
</fC03>
<fC03 i1="03" i2="X" l="FRE"><s0>Samarium II Iodure</s0>
<s2>NC</s2>
<s2>NA</s2>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="ENG"><s0>Samarium II Iodides</s0>
<s2>NC</s2>
<s2>NA</s2>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="SPA"><s0>Samario II Ioduro</s0>
<s2>NC</s2>
<s2>NA</s2>
<s5>03</s5>
</fC03>
<fC03 i1="04" i2="X" l="FRE"><s0>Indium</s0>
<s2>NC</s2>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="ENG"><s0>Indium</s0>
<s2>NC</s2>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="SPA"><s0>Indio</s0>
<s2>NC</s2>
<s5>04</s5>
</fC03>
<fC03 i1="05" i2="X" l="FRE"><s0>Composé nitro</s0>
<s2>FX</s2>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="ENG"><s0>Nitro compound</s0>
<s2>FX</s2>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="SPA"><s0>Compuesto nitro</s0>
<s2>FX</s2>
<s5>05</s5>
</fC03>
<fC03 i1="06" i2="X" l="FRE"><s0>Aldéhyde</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="ENG"><s0>Aldehyde</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="SPA"><s0>Aldehído</s0>
<s5>06</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE"><s0>Métal</s0>
<s2>NC</s2>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="ENG"><s0>Metal</s0>
<s2>NC</s2>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="SPA"><s0>Metal</s0>
<s2>NC</s2>
<s5>07</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE"><s0>Diastéréoisomère</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG"><s0>Diastereomer</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA"><s0>Diasteréomero</s0>
<s5>08</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE"><s0>Effet stérique</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG"><s0>Steric effect</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Efecto estérico</s0>
<s5>09</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE"><s0>Encombrement stérique</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG"><s0>Steric hindrance</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA"><s0>Embarazo estérico</s0>
<s5>10</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE"><s0>Aldolisation</s0>
<s5>41</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG"><s0>Aldol condensation</s0>
<s5>41</s5>
</fC03>
<fC03 i1="11" i2="X" l="SPA"><s0>Aldolización</s0>
<s5>41</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE"><s0>Lanthanide Composé</s0>
<s2>NC</s2>
<s2>NA</s2>
<s5>42</s5>
</fC03>
<fC03 i1="12" i2="X" l="ENG"><s0>Lanthanide Compounds</s0>
<s2>NC</s2>
<s2>NA</s2>
<s5>42</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA"><s0>Lantánido Compuesto</s0>
<s2>NC</s2>
<s2>NA</s2>
<s5>42</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Réaction de Henry</s0>
<s4>CD</s4>
<s5>96</s5>
</fC03>
<fC03 i1="13" i2="X" l="ENG"><s0>Henry reaction</s0>
<s4>CD</s4>
<s5>96</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>Réaction Henry</s0>
<s4>CD</s4>
<s5>97</s5>
</fC03>
<fC03 i1="14" i2="X" l="ENG"><s0>Henry reaction</s0>
<s4>CD</s4>
<s5>97</s5>
</fC03>
<fN21><s1>324</s1>
</fN21>
<fN44 i1="01"><s1>OTO</s1>
</fN44>
<fN82><s1>OTO</s1>
</fN82>
</pA>
</standard>
</inist>
</record>

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Synthesis of Sugar-Derived 2-Nitroalkanols via Henry Reaction Promoted by Samarium Diiodide or Indium

Synthesis of Sugar-Derived 2-Nitroalkanols via Henry Reaction Promoted by Samarium Diiodide or Indium

Descripteurs français

English descriptors

Abstract

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Links to Exploration step

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

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