The intramolecular aza-Michael reaction of carbamates bearing remote alpha,beta-unsaturated aldehydes under organocatalytic conditions took place with good yields and excellent ee's when Jørgensen catalyst IV was used in the process, giving rise to the enantioselective formation of several five- and six-membered heterocycles. The developed methodology was applied to the synthesis of three piperidine alkaloids.
A highly stereoselective synthesis of fluorinated 1,3-disubstituted isoindolines is described. To this end, a tandem reaction consisting of a diastereoselective addition of fluorinated nucleophiles to Ellman's N-(tert-butanesulfinyl)imines followed by an intramolecular aza-Michael reaction has been developed. This strategy allows for the construction of isoindolines bearing several degrees of fluorination (mono-, di-, or trifluoromethyl as well as heavier fluorinated groups). In the majority of all cases, the products are formed as single isomers.
Die Diffusion von NO‐Gas in Kristalle aus [(TPP)Fe(H2O)]SO3CF3 (1) führt zur Nitrosylierung der Hälfte aller Moleküle unter Bildung von [(TPP)Fe(NO)(H2O)]SO3CF3 (2). Diese Festphasenreaktion geht mit einer deutlichen Verschiebung der Porphyrine einher, um Platz für die NO‐Liganden zu schaffen. Weil beide Molekülarten in demselben Kristall vorliegen, können ihre geometrischen Parameter direkt verglichen werden. TPP=Tetraphenylporphyrin; C schwarz, N blau, O rot.
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