36 research outputs found

    Electrochemically induced diastereoselective functionalization of N-acyloxazolidin-2-ones

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    The electrochemical generation of chiral enolates is here described, either by cathodic reduction of a C-Br bond or using electrogenerated acetonitrile anion. The reactivity of these enolates have been studied in carboxylation, alkylation and conjugate addiction reactions, obtaining in some cases a good diastereoselectivity

    Electrochemically induced Knoevenagel condensation in solvent- and supporting electrolyte-free conditions

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    Solvent- and supporting electrolyte-free electrochemically induced Knoevenagel condensation of malononitrile with aldehydes or ketones, at 40 uC, yields ylidenemalononitriles in high yields

    A safe and mild synthesis of organic carbonates from alkyl halides and tetrabutylammonium alkyl carbonates

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    A safe and mild procedure for the synthesis of mixed organic carbonates is described. Reaction of com- mercially available tetrabutylammonium methoxide and ethoxide with carbon dioxide yields the corresponding meth- yl and ethyl tetrabutylammonium carbonates (TBAMC and TBAEC). The reactions of these new compounds with several different alkyl halides give methyl and ethyl carbonates in high yields. The use of classic toxic and harmful chemicals such as phosgene and carbon monoxide is avoided

    An innovative strategy for electrochemically-promoted addition reaction

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    A new strategy based on the catalytic release of the supporting electrolyte agent in the electrolysis medium proved to be effective for the direct electroactivation of suitable C–H acid- containing compounds vs. catalytic addition processes, under solvent-free conditions

    Electrochemical generation of chiral oxazolidin-2-ones anions: a new procedure for the highly diastereoselective conjugate addition to nitroalkenes

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    A mild and efficient electrochemical alternative to classical base-catalyzed conjugate addition of nitrogen nucleophiles is reported here. The cleavage of the carbamic N . H bond of Evans' chiral auxiliaries can be very efficiently performed by electrolysis under galvanostatic control and the resulting naked anions used for highly, diastereoselective conjugate addition to nitroalkenes. The degree of stereoselectivity was shown to depend on the steric hindrance of the group at the ring C(4) of the starting oxazolidin-2-one. (C) 2001 Elsevier Science Ltd. All rights reserved
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