ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
α-Amino Acids as Nucleophilic Acyl Equivalents, V. Sterically Directed Michael-Addition of Oxazolin-5-one Anions to Activated Double Bonds; Synthesis of 1-4-Dicarbonyl compounds and γ-OxonitrilesOxazolin-5-ones with bulky substituents like mesityl or 1-butylcyclohexyl at C-2 undergo triethyl-amine catalyzed addition to activated olefins exclusively at C-4. Hydrolysis of the derived 4,4-disubstituted 2-mesityl-2-oxazolin-5-ones 9 leads to N-mesitoyl amino acids 10 which yield 1,4-dicarbonyl compounds or γ-oxonitriles 11 on oxidation with lead tetraacetate.
Notes:
Oxazolin-5-one, die in 2-Stellung raumerfüllende Reste wie Mesityl oder 1-Butylcyclohexyl tragen, addieren in Gegenwart von Triethylamin aktivierte Olefine ausschließlich in 4-Stellung. Die so erhaltenen 4,4-disubstituierten 2-Mesityl-2-oxazolin-5-one 9 werden nach Hydrolyse zu den N-Mesitoylaminosäuren 10 mit Bleitetraacetat zu 1,4-Dicarbonylverbindungen oder γ-Oxonitrilen 11 oxidiert.
Additional Material:
7 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19811140721
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