Has-Becker, Senay and Bodmann, Kerstin and Kreuder, Reinhard and Santoni, Gabriella and Rein, Tobias and Reiser, Oliver (2001) High-Pressure Induced Domino-Horner-Wadsworth-Emmons (HWE) -Michael Reactions. Synlett 2001 (9), pp. 1395-1398.
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A new protocol for the alkenylation of carbonyl compounds with phosphonates (Horner-Wadsworth-Emmons reaction) is described. Aldehydes react with phosphonates already at room temperature in the presence of triethylamine without further activation by Lewis-acids if high-pressure (8 kbar) is applied to the system. Based on this protocol a domino process was developed combining the HWE reaction with a Michael reaction, thus allowing the one-pot synthesis of β-amino esters, β-thio esters or β-thio nitriles.
|Institutions:||Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser|
|Keywords:||Horner-Wadsworth-Emmons reaction; Michael addition; domino reaction; β-amino esters; β-thio esters; β-thio nitriles; high-pressure|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Owner:||Helge Knüttel (ADMIN)|
|Deposited On:||01 Sep 2006|
|Last Modified:||05 Aug 2009 13:22|