52398-45-5Relevant articles and documents
Methoxycarbonylmethylation of aldehydes via siloxycyclopropanes: Methyl 3,3-dimethyl-4-oxobutanoate
Reissig, Hans-Ulrich,Reichelt, Ingrid,Kunz, Thomas
, p. 189 - 189 (2017/06/01)
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Catalytic Hydrogenolysis of Methyl 2-Siloxycyclopropanecarboxylates: Investigations Regarding Chemoselectivity, Regioselectivity, and Stereoselectivity
Brueckner, Christiane,Reissig, Hans-Ulrich
, p. 617 - 626 (2007/10/02)
Alkyl-substituted methyl 2-(trimethylsiloxy)cyclopropanecarboxylates 8a - 8f are opened by hydrogen in the presence of palladium on carbon affording 4-oxoalkanoic esters 10a - 10e by desilylation. 2-Phenyl-substituted cyclopropanes 8g - 8j, however, provide 4-phenylbutanoic esters 13g - 13j under these conditions.Formation of 13j is not stereoselective.Here the primary cyclopropane cleavage is followed by hydrogenolysis of the benzylic C-O bond.This subsequent reaction can be suppressed in the case of 8g by poisoning the catalyst with triethylamine; otherwise the tert-butyldimethylsiloxy compounds 11g - 11i have to be used.Butanoic esters 14h and 14i, respectively, are formed as mixtures of diastereomeres, which is another indication for nonstereoselective hydrogenolysis of cyclopropanes.Whereas slow desilylation by hydrogen was observed with the 3-phenyl-substituted cyclopropane derivative 8k, the vinylcyclopropane 8m in part suffers cleavage of the 1-3 bond of the three-membered ring.Regio- and stereoselectivity of the hydrogenolysis of the donor-acceptor-substituted cyclopropanes 8 and 11 are discussed.
Donor-acceptor-substituierte Cyclopropane: Synthese und Ringoeffnung zu 1,4-Dicarbonylverbindungen
Reissig, Hans-Ulrich,Hirsch, Elisabeth
, p. 839 - 840 (2007/10/02)
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