37996-41-1Relevant articles and documents
A Very Large Stereoelectronic Effect on Acetal Cleavage
Evans, Christopher M.,Glenn, Robert,Kirby, Anthony J.
, p. 4706 - 4707 (1982)
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Conformationally restricted nonchiral pipecolic acid analogues
Radchenko, Dmytro S.,Kopylova, Nataliya,Grygorenko, Oleksandr O.,Komarov, Igor V.
scheme or table, p. 5541 - 5544 (2009/12/04)
(Chemical Equation Presented) Practical syntheses of 2-azabicyclo[3.1.1] heptane-1-carboxylic (2,4-methanopipecolic), 2-azabicyclo [2.2.2]octane-1- carboxylic (2,5-ethanopipecolic), and 9-azabicyclo[3.3.1]nonane-1-carboxylic (2,6-propanopipecolic) acids a
Intramolecular C-H insertion reactions of (η5-Cyclopentadienyl)dicarbonyliron carbene complexes: Scope of the reactions and application to the synthesis of (±)-sterpurene and (±)-pentalenene
Ishii,Zhao,Mehta,Knors,Helquist
, p. 3449 - 3458 (2007/10/03)
(η5-Cyclopentadienyl)dicarbonyliron carbene complexes, [(η5C5H5) (CO)2Fe=CHR]+BF4-, are generated as reactive intermediates from thioether derivatives, (η5-C5H5)(CO)2FeCH(R)SPh, by S-alkylation with trimethyloxonium tetrafluoroborate and loss of thioanisole. The carbene complexes undergo intramolecular C-H insertion into appropriately situated side chains to form cyclopentane derivatives. The reaction has been developed into a general procedure employing cycloalkanones as scaffolds bearing the iron carbene moieties and the side chains at C(2) and C(3), respectively. The products of the intramolecular insertion reactions are substituted bicyclo[n.3.0]alkanones. The scope and limitations of the reaction are described. The reaction is applied to a total synthesis of sterpurene and to a formal synthesis of pentalenene. Overall, this approach to cyclopentane annulation complements the related metal-catalyzed insertion reactions of diazocarbonyl compounds, which are also believed to occur via metal carbene complexes.