Indium (III) mediated Markovnikov addition of malonates and β-ketoesters to terminal alkynes and the formation of Knoevenagel condensation products

The indium(III) triflate mediated addition of active methylene compounds to terminal alkynes has been expanded to use malonates and low boiling terminal alkynes to form the Markovnikov addition products. Indium(III) chloride and indium(III) bromide were also found to be efficient catalysts. Knoevena...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 61; no. 32; pp. 7807 - 7813
Main Authors Zhang, Ji, Blazecka, Peter G., Angell, Paul, Lovdahl, Mark, Curran, Timothy T.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.08.2005
Elsevier
Subjects
Active methylene
Alkyne
Chemistry
Chemistry, Organic
Indium (III)
Knoevenagel
Markovnikov
Physical Sciences
Science & Technology
Markovnikov
Active methylene
Indium (III)
Knoevenagel
Alkyne
CATALYTIC ENANTIOSELECTIVE SYNTHESIS
ORGANIC-SYNTHESIS
DOMINO REACTIONS
active methylene
OLEFIN CROSS-METATHESIS
CYCLIC ENOL ETHERS
HIGHLY EFFICIENT
indium (III)
RING-CLOSING METATHESIS
DIASTEREOSELECTIVE SYNTHESIS
KETO-ESTERS
alkyne
WATER
Online AccessGet full text

Cover

More Information
Summary:The indium(III) triflate mediated addition of active methylene compounds to terminal alkynes has been expanded to use malonates and low boiling terminal alkynes to form the Markovnikov addition products. Indium(III) chloride and indium(III) bromide were also found to be efficient catalysts. Knoevenagel condensation products were isolated when reactions involved a simple malonate or β-ketoester. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.05.065