Nickel-Catalyzed Reductive Coupling of Dienes and Carbonyl Compounds
Identifieur interne : 000002 ( Main/Exploration ); précédent : 000001; suivant : 000003Nickel-Catalyzed Reductive Coupling of Dienes and Carbonyl Compounds
Auteurs : RBID : ISTEX:978-3-540-72879-5_Chapter_121.pdfEnglish descriptors
- KwdEn :
Abstract
Nickel-catalyzed allylation and homoallylation of carbonyl compounds with conjugated dienes promoted by a several kind of organometallic reagents are described. In the presence of Ni(cod)2, trialkylsilanes (R3SiH) serve as reducing agents and promote ω-dienyl aldehydes to undergo intramolecular allylation with high regio- and stereoselectivity. In the presence of indium(I) iodide, Ni(acac)2 catalyzes double allylation of aldehydes with 1,3-butadiene to provide 3-hexene-1,6-diols and/or 2-vinyl-1,4-butanediols. The combination of Ni(acac)2 and triethylborane selectively promotes homoallylation of aromatic aldehydes and α,β-unsaturated aldehydes. The reaction shows high regio- and stereoselectivity. Isoprene, for example, provides 1-substituted 3-methyl-4-pentenols with excellent 1,3-anti stereoselectivity. Diethylzinc, in place of Et3B, nicely promotes the homoallylation of less reactive carbonyl compounds (sterically congested aliphatic aldehydes and ketones). 1,3-Cyclohexadiene is one exception among the dienes examined and undergoes allylation instead of homoallylation under the catalysis of Ni-Et2Zn. Aldimines prepared in situ from aldehydes and p-anisidine undergo homoallylation with 2-substituted-1,3-deines under Ni-Et2Zn catalysis to afford bis-homoallyl amines with excellent 1,3-syn stereoselectivity.
DOI: 10.1007/128_2007_121
Links toward previous steps (curation, corpus...)
Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title>Nickel-Catalyzed Reductive Coupling of Dienes and Carbonyl Compounds</title><author><name>Masanari Kimura</name><affiliation wicri:level="1"><mods:affiliation>Graduate School of Science and Technology, Nagasaki University, 1-14 Bunkyo, 852-8521, Nagasaki, Japan</mods:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Graduate School of Science and Technology, Nagasaki University, 1-14 Bunkyo, 852-8521, Nagasaki</wicri:regionArea><wicri:noRegion>Nagasaki</wicri:noRegion></affiliation></author><author><name>Yoshinao Tamaru</name><affiliation wicri:level="1"><mods:affiliation>Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo, 852-8521, Nagasaki, Japan</mods:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo, 852-8521, Nagasaki</wicri:regionArea><wicri:noRegion>Nagasaki</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="RBID">ISTEX:978-3-540-72879-5_Chapter_121.pdf</idno><date when="2007">2007</date><idno type="doi">10.1007/128_2007_121</idno><idno type="wicri:Area/Main/Corpus">000932</idno><idno type="wicri:Area/Main/Curation">000932</idno><idno type="wicri:Area/Main/Exploration">000002</idno></publicationStmt><seriesStmt><idno type="doi">10.1007/978-3-540-72879-5</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Allylation</term><term>Carbonyl compound</term><term>Dienes</term><term>Homoallylation</term><term>Nickel catalysis</term><term>Reductive coupling </term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="eng">Nickel-catalyzed allylation and homoallylation of carbonyl compounds with conjugated dienes promoted by a several kind of organometallic reagents are described. In the presence of Ni(cod)2, trialkylsilanes (R3SiH) serve as reducing agents and promote ω-dienyl aldehydes to undergo intramolecular allylation with high regio- and stereoselectivity. In the presence of indium(I) iodide, Ni(acac)2 catalyzes double allylation of aldehydes with 1,3-butadiene to provide 3-hexene-1,6-diols and/or 2-vinyl-1,4-butanediols. The combination of Ni(acac)2 and triethylborane selectively promotes homoallylation of aromatic aldehydes and α,β-unsaturated aldehydes. The reaction shows high regio- and stereoselectivity. Isoprene, for example, provides 1-substituted 3-methyl-4-pentenols with excellent 1,3-anti stereoselectivity. Diethylzinc, in place of Et3B, nicely promotes the homoallylation of less reactive carbonyl compounds (sterically congested aliphatic aldehydes and ketones). 1,3-Cyclohexadiene is one exception among the dienes examined and undergoes allylation instead of homoallylation under the catalysis of Ni-Et2Zn. Aldimines prepared in situ from aldehydes and p-anisidine undergo homoallylation with 2-substituted-1,3-deines under Ni-Et2Zn catalysis to afford bis-homoallyl amines with excellent 1,3-syn stereoselectivity. </div></front></TEI><mods xsi:schemaLocation="http://www.loc.gov/mods/v3 file:///applis/istex/home/loadistex/home/etc/xsd/mods.xsd" version="3.4" istexId="a2842552b14ca3e2a2724e234d3b1abfb10de788"><titleInfo lang="eng"><title>Nickel-Catalyzed Reductive Coupling of Dienes and Carbonyl Compounds</title></titleInfo><name type="personal"><namePart type="given">Masanari</namePart><namePart type="family">Kimura</namePart><role><roleTerm type="text">author</roleTerm></role><affiliation>Graduate School of Science and Technology, Nagasaki University, 1-14 Bunkyo, 852-8521, Nagasaki, Japan</affiliation></name><name type="personal"><namePart type="given">Yoshinao</namePart><namePart type="family">Tamaru</namePart><role><roleTerm type="text">author</roleTerm></role><description>tamaru@nagasaki-u.ac.jp</description><affiliation>Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo, 852-8521, Nagasaki, Japan</affiliation></name><typeOfResource>text</typeOfResource><genre>Original Paper</genre><originInfo><publisher>Springer Berlin Heidelberg, Berlin, Heidelberg</publisher><copyrightDate encoding="w3cdtf">2007</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType></physicalDescription><abstract lang="eng">Nickel-catalyzed allylation and homoallylation of carbonyl compounds with conjugated dienes promoted by a several kind of organometallic reagents are described. In the presence of Ni(cod)2, trialkylsilanes (R3SiH) serve as reducing agents and promote ω-dienyl aldehydes to undergo intramolecular allylation with high regio- and stereoselectivity. In the presence of indium(I) iodide, Ni(acac)2 catalyzes double allylation of aldehydes with 1,3-butadiene to provide 3-hexene-1,6-diols and/or 2-vinyl-1,4-butanediols. The combination of Ni(acac)2 and triethylborane selectively promotes homoallylation of aromatic aldehydes and α,β-unsaturated aldehydes. The reaction shows high regio- and stereoselectivity. Isoprene, for example, provides 1-substituted 3-methyl-4-pentenols with excellent 1,3-anti stereoselectivity. Diethylzinc, in place of Et3B, nicely promotes the homoallylation of less reactive carbonyl compounds (sterically congested aliphatic aldehydes and ketones). 1,3-Cyclohexadiene is one exception among the dienes examined and undergoes allylation instead of homoallylation under the catalysis of Ni-Et2Zn. Aldimines prepared in situ from aldehydes and p-anisidine undergo homoallylation with 2-substituted-1,3-deines under Ni-Et2Zn catalysis to afford bis-homoallyl amines with excellent 1,3-syn stereoselectivity. </abstract><subject lang="eng"><topic>Allylation</topic><topic>Carbonyl compound</topic><topic>Dienes</topic><topic>Homoallylation</topic><topic>Nickel catalysis</topic><topic>Reductive coupling </topic></subject><relatedItem type="series"><titleInfo><title>Topics in Current Chemistry</title><subTitle>A Departure from Preformed Organometallic Reagents</subTitle><partNumber>Year: 2007</partNumber><partNumber>Volume: 279</partNumber><partName lang="eng">Metal Catalyzed Reductive C–C Bond Formation [A Departure from Preformed Organometallic Reagents]</partName></titleInfo><genre>Reviews</genre><genre>eBook</genre><originInfo><copyrightDate encoding="w3cdtf">2007</copyrightDate><issuance>monographic</issuance></originInfo><subject usage="primary"><topic>Chemistry</topic><topic>Organic Chemistry</topic><topic>Organometallic Chemistry</topic></subject><identifier type="issn">0340-1022</identifier><identifier type="issn">Electronic: 1436-5049</identifier><identifier type="isbn">978-3-540-72878-8</identifier><identifier type="isbn">Electronic: 978-3-540-72879-5</identifier><identifier type="doi">10.1007/978-3-540-72879-5</identifier><identifier type="matrixNumber">128</identifier><identifier type="local">BookChapterCount: 8</identifier><identifier type="local">BookTitleID: 140573</identifier><recordInfo><recordOrigin>Springer-Verlag Berlin Heidelberg, 2007</recordOrigin></recordInfo></relatedItem><identifier type="doi">10.1007/128_2007_121</identifier><identifier type="matrixNumber">Chap7</identifier><identifier type="local">121</identifier><accessCondition type="use and reproduction">MetadataGrant: OpenAccess</accessCondition><accessCondition type="use and reproduction">AbstractGrant: OpenAccess</accessCondition><accessCondition type="restriction on access">BodyPDFGrant: Restricted</accessCondition><accessCondition type="restriction on access">BodyHTMLGrant: Restricted</accessCondition><accessCondition type="restriction on access">BibliographyGrant: Restricted</accessCondition><accessCondition type="restriction on access">ESMGrant: Restricted</accessCondition><part><extent unit="pages"><start>173</start><end>207</end></extent></part><recordInfo><recordOrigin>Springer-Verlag Berlin Heidelberg, 2007</recordOrigin><recordIdentifier>978-3-540-72879-5_Chapter_121.pdf</recordIdentifier></recordInfo></mods></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=IndiumV1/Data/Main/Exploration
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000002 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 000002 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= *** parameter Area/wikiCode missing ***
|area= IndiumV1
|flux= Main
|étape= Exploration
|type= RBID
|clé= ISTEX:978-3-540-72879-5_Chapter_121.pdf
|texte= Nickel-Catalyzed Reductive Coupling of Dienes and Carbonyl Compounds
}}
| This area was generated with Dilib version V0.5.81. |  |