The Diels-Alder reaction between deactivated dienes and electron-deficient dienophiles on solid support: Stereoselective synthesis of hexahydro-1,3- dioxoisoindoles

Journal of Combinatorial Chemistry

Volumn 6, Issue 2, 2004, Pages 283-285

  Kiriazis, Alexandros ^a   Leikoski, Tuomo ^a   Mutikainen, Ilpo ^a   Yli Kauhaluoma, Jari ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; INDOLE DERIVATIVE; MALEIMIDE DERIVATIVE; RESIN; SOLVENT; TOLUENE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; ELECTRON; HEAT TREATMENT; INHIBITION KINETICS; QUANTUM YIELD; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 1842611075     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc030114h     Document Type: Article

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23. Diazomethane was prepared as described in the Aldrich Technical Bulletin AL-180, Diazald, MNNG and Diazomethane Generators.
24. Our tentative proposal is that diazomethane might be capable of acting as a weak base and epimerizing the cycloadducts 3a-h by means of abstraction of the acidic α-protons from 3a-h, enolization, and reprotonation of the enolate in the course of the diazomethane-assisted methylation.
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