Intramolecular Baylis-Hillman reaction: synthesis of heterocyclic molecules
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چکیده
منابع مشابه
Bifunctional ferrocene-based squaramide-phosphine as an organocatalyst for highly enantioselective intramolecular Morita-Baylis-Hillman reaction.
This work demonstrates that, in accord with metal catalysis, ferrocene could be an excellent scaffold for organocatalysts. The simple and easily accessible bifunctional ferrocene-based squaramide-phosphine shows high enantioselectivity in the intramolecular Morita-Baylis-Hillman reaction of 7-aryl-7-oxo-5-heptenals, giving a variety of 2-aroyl-2-cyclohexenols in up to 96% ee.
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...
متن کاملMorita–Baylis–Hillman reaction of acrylamide with isatin derivatives
The Morita-Baylis-Hillman reaction of acrylamide, as an activated alkene, has seen little development due to its low reactivity. We have developed the reaction using isatin derivatives with acrylamide, DABCO as a promoter and phenol as an additive in acetonitrile. The corresponding aza version with acrylate and acrylonitrile has also been developed resulting in high product yields.
متن کاملApplication 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...
متن کاملEnantioselective, organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman reactions: stereochemical issues.
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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ژورنال
عنوان ژورنال: Arkivoc
سال: 2015
ISSN: 1551-7012
DOI: 10.3998/ark.5550190.p009.322