Concise and Stereoselective Synthesis of Enamides and Dienamides by a Titanium-Mediated Coupling Method

Ynamide−titanium alkoxide complexes underwent hydrolysis or addition to aldehydes and ketones to give single, stereodefined di- or trisubstituted enamides in good yields. Alternatively, coupling of a variety of alkyne−titanium alkoxide complexes with terminal ynamides generated amino-substituted tit...

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Published inOrganic letters Vol. 5; no. 1; pp. 67 - 70
Main Authors Tanaka, Ryoichi, Hirano, Shuji, Urabe, Hirokazu, Sato, Fumie
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 09.01.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
ALKYNE COMPLEXES
ZIRCONACYCLE PHOSPHONATES
DIELS-ALDER REACTIONS
ISOMERIZATION
RUTHENIUM COMPLEXES
CHEMISTRY
STEREOSPECIFIC SYNTHESIS
PAUSON-KHAND REACTIONS
METAL-COMPLEXES
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Summary:Ynamide−titanium alkoxide complexes underwent hydrolysis or addition to aldehydes and ketones to give single, stereodefined di- or trisubstituted enamides in good yields. Alternatively, coupling of a variety of alkyne−titanium alkoxide complexes with terminal ynamides generated amino-substituted titanacyclopentadienes, hydrolysis or aldehyde addition of which afforded stereodefined dienamides.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027209x