Reactions of diazoalkanes with unsaturated compounds 16. Catalytic reactions of diazomethane with 2-alkenyl-1,3-oxazolidines and 2-alkenyl-1,3-oxathiolanes

Autor: V. A. Dokichev, M. D. Khanova, R. Z. Biglova, R. R. Rafikov, I. P. Baykova, Yu. V. Tomilov, Rimma M. Sultanova
Rok vydání: 2008
Předmět:
Zdroj: Russian Chemical Bulletin. 57:617-621
ISSN: 1573-9171
1066-5285
DOI: 10.1007/s11172-008-0097-5
Popis: The influence of 1,3-oxazolidine and 1,3-oxathiolane fragments in substituted alkenes on the direction of their catalytic reaction with diazomethane has been investigated. The olefins bearing an oxazolidine substituent in the α- or γ-position and an oxathiolane substituent in the γ-position relative to the C=C bond react with diazomethane in the presence of Pd(acac)2 selectively resulting in cyclopropanation products. The use of Cu(OTf)2 does not result in cyclopropanation; however Cu(OTf)2 catalyzes the reaction of diazomethane with 2-(alk-1-enyl)-1,3-oxathiolanes yielding 2,3,5,6-tetrahydro-1,4-oxathiocines formed through the [2,3]-sigmatropic rearrangement of the intermediate sulfonium ylides.
Databáze: OpenAIRE
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