A New Entry to Enantioselective Synthesis of .ALPHA.-Methylene-.BETA.-hydroxy Ketones by the Chalcogeno-Baylis-Hillman Reaction.
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چکیده
منابع مشابه
Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction
7-Azaisatin and 7-azaoxindole skeletons are valuable building blocks in diverse biologically active substances. Here 7-azaisatins turned out to be more efficient electrophiles than the analogous isatins in the enantioselective Morita-Baylis-Hillman (MBH) reactions with maleimides using a bifunctional tertiary amine, β-isocupreidine (β-ICD), as the catalyst. This route allows a convenient approa...
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En route to a photoswitchable interlocked catalyst we have proved the ability of thiodiglycolamide to act as a template in the formation of hydrogen-bonded [2]rotaxanes. X-ray diffraction studies reveal the shielding of the sulfide atom by the macrocycle. A series of molecular shuttles are described as having an isomerizable fumaramide and thiodiglycolamide binding sites for controlling the rel...
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Conscious of the importance that stereochemical issues may have on the design of efficient organocatalyts for both Morita-Baylis-Hillman and aza-Morita-Baylis-Hillman reaction we have analyzed them in this minireview. The so-called standard reactions involve "naked" enolates which therefore should lead to the syn adducts as the major products, irrespective of the E, Z stereochemistry of the eno...
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Chagas disease, caused by the protozoan Trypanosoma cruzi, remains a serious health concern due to the lack of effective vaccines or satisfactory treatment. In the search for new compounds against this neglected disease, we have previously demonstrated that the compound 3-Hydroxy-2-methylene-3-(4-nitrophenylpropanenitrile) (MBHA3), derived from the Morita-Baylis-Hillman reaction, effectively ca...
متن کاملProbing the mechanism of Baylis-Hillman reaction in ionic liquids.
The kinetic data for a Baylis-Hillman reaction in certain ionic liquids possessing ethylsulfate anion [EtSO(4)](-) demonstrate that the rate determining step (RDS) is second order in aldehyde, but first order in acrylate and DABCO. This observation is similar to the one made by McQuade et al., who carried out this reaction in an aprotic polar solvent like DMSO. However, this is in contrast to t...
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ژورنال
عنوان ژورنال: Chemical and Pharmaceutical Bulletin
سال: 1999
ISSN: 0009-2363,1347-5223
DOI: 10.1248/cpb.47.956