High-pressure induced Domino-Horner-Wadsworth-Emmons (HWE) Michael reactions

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. ISSN 0936-5214

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Abstract

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 beta -amino esters, beta -thio esters or beta -thio nitriles.

Item Type: Article
Uncontrolled Keywords: DIELS-ALDER REACTIONS; ORGANIC-REACTIONS; WITTIG REACTIONS; ENAMINO KETONES; DIASTEREOSELECTIVITY; REACTIVITY; ACTIVATION; ESTERS; ENANTIOSELECTIVITY; CYCLOADDITIONS; Horner-Wadsworth-Emmons reaction; Michael addition; domino reaction; beta-amino esters; beta-thio esters; beta-thio nitriles; high-pressure
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 16 Aug 2023 09:53
Last Modified: 16 Aug 2023 09:53
URI: https://pred.uni-regensburg.de/id/eprint/41176

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