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Synlett 2001; 2001(9): 1395-1398
DOI: 10.1055/s-2001-16786
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High-Pressure Induced Domino-Horner-Wadsworth-Emmons (HWE) - Michael Reactions

Senay Has-Becker* , Kerstin Bodmann, Reinhard Kreuder, Gabriella Santoni, Tobias Rein, Oliver Reiser
  • *Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany; Fax + 49-94 19 43 41 21; E-mail: Oliver.Reiser@chemie.uni-regensburg.de
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Publication Date:
28 August 2001 (online)

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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.

Horner-Wadsworth-Emmons reaction - Michael addition - domino reaction - β-amino esters - β-thio esters - β-thio nitriles - high-pressure

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