Nickel-Catalyzed Highly Regioselective Multicomponent Coupling of Ynamides, Aldehydes, and Silane: A New Access to Functionalized Enamides

A new method for preparation of functionalized enamides by a nickel-catalyzed multicomponent coupling of ynamides, aldehydes, and silane has been developed. The coupling reaction proceeded in the presence of a nickel-IMes catalyst to give the corresponding γ-silyloxyenamide derivative, which has an...

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Published inOrganic letters Vol. 10; no. 17; pp. 3829 - 3832
Main Authors Saito, Nozomi, Katayama, Tomoyuki, Sato, Yoshihiro
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.09.2008
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Alkenes - chemical synthesis
Alkynes - chemistry
Amides - chemical synthesis
Catalysis
Chemistry
Chemistry, Organic
Models, Molecular
Nickel - chemistry
Oxazolidinones - chemistry
Physical Sciences
Science & Technology
Silanes - chemistry
ALKENES
1,3-DIENES
REDUCTIVE COUPLINGS
SELECTIVE ISOMERIZATION
N-HETEROCYCLIC CARBENES
STEREOSELECTIVE-SYNTHESIS
LIGAND
ALKYNES
OXIDATIVE AMINATION
RUTHENIUM COMPLEX
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Summary:A new method for preparation of functionalized enamides by a nickel-catalyzed multicomponent coupling of ynamides, aldehydes, and silane has been developed. The coupling reaction proceeded in the presence of a nickel-IMes catalyst to give the corresponding γ-silyloxyenamide derivative, which has an allylic alcohol moiety in the molecule, in a highly stereoselective manner.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol801534e