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- Aldol_reaction abstract "The aldol reaction is a means of forming carbon–carbon bonds in organic chemistry.Discovered independently by Charles-Adolphe Wurtz and Alexander Borodin in 1872, the reaction combines two carbonyl compounds (the original experiments used aldehydes) to form a new β-hydroxy carbonyl compound. These products are known as aldols, from the aldehyde + alcohol, a structural motif seen in many of the products. Aldol structural units are found in many important molecules, whether naturally occurring or synthetic.For example, the aldol reaction has been used in the large-scale production of the commodity chemical pentaerythritoland the synthesis of the heart disease drug Lipitor (atorvastatin, calcium salt).The aldol reaction unites two relatively simple molecules into a more complex one. Increased complexity arises because up to two new stereogenic centers (on the α- and β-carbon of the aldol adduct, marked with asterisks in the scheme below) are formed. Modern methodology is capable of not only allowing aldol reactions to proceed in high yield but also controlling both the relative and absolute stereochemical configuration of these stereocenters. This ability to selectively synthesize a particular stereoisomer is significant because different stereoisomers can have very different chemical and biological properties.For example, stereogenic aldol units are especially common in polyketides, a class of molecules found in biological organisms. In nature, polyketides are synthesized by enzymes that effect iterative Claisen condensations. The 1,3-dicarbonyl products of these reactions can then be variously derivatized to produce a wide variety of interesting structures. Often, such derivitization involves the reduction of one of the carbonyl groups, producing the aldol subunit. Some of these structures have potent biological properties: the immunosuppressant FK506, the anti-tumor agent discodermolide, or the antifungal agent amphotericin B, for example. Although the synthesis of many such compounds was once considered nearly impossible, aldol methodology has allowed their efficient synthesis in many cases.A typical modern aldol addition reaction, shown above, might involve the nucleophilic addition of a ketone enolate to an aldehyde. Once formed, the aldol product can sometimes lose a molecule of water to form an α,β-unsaturated carbonyl compound. This is called aldol condensation. A variety of nucleophiles may be employed in the aldol reaction, including the enols, enolates, and enol ethers of ketones, aldehydes, and many other carbonyl compounds. The electrophilic partner is usually an aldehyde or ketone (many variations, such as the Mannich reaction, exist). When the nucleophile and electrophile are different, the reaction is called a crossed aldol reaction; on the converse, when the nucleophile and electrophile are the same, the reaction is called an aldol dimerization.".
- Aldol_reaction thumbnail Typical_aldol-en.svg?width=300.
- Aldol_reaction wikiPageExternalLink JJB%20Aldol%20Lecture%2021%20Final.pdf.
- Aldol_reaction wikiPageID "498127".
- Aldol_reaction wikiPageLength "53311".
- Aldol_reaction wikiPageOutDegree "228".
- Aldol_reaction wikiPageRevisionID "705679966".
- Aldol_reaction wikiPageWikiLink 2-Oxazolidone.
- Aldol_reaction wikiPageWikiLink Acetoxy_group.
- Aldol_reaction wikiPageWikiLink Acyl.
- Aldol_reaction wikiPageWikiLink Acylation.
- Aldol_reaction wikiPageWikiLink Addition_reaction.
- Aldol_reaction wikiPageWikiLink Aldehyde.
- Aldol_reaction wikiPageWikiLink Aldol.
- Aldol_reaction wikiPageWikiLink Aldol_condensation.
- Aldol_reaction wikiPageWikiLink Aldolase_A.
- Aldol_reaction wikiPageWikiLink Aldol–Tishchenko_reaction.
- Aldol_reaction wikiPageWikiLink Alexander_Borodin.
- Aldol_reaction wikiPageWikiLink Alkoxide.
- Aldol_reaction wikiPageWikiLink Allose.
- Aldol_reaction wikiPageWikiLink Allylic_strain.
- Aldol_reaction wikiPageWikiLink Alpha_and_beta_carbon.
- Aldol_reaction wikiPageWikiLink Aluminium.
- Aldol_reaction wikiPageWikiLink Amine.
- Aldol_reaction wikiPageWikiLink Amphotericin_B.
- Aldol_reaction wikiPageWikiLink Asymmetric_induction.
- Aldol_reaction wikiPageWikiLink Atorvastatin.
- Aldol_reaction wikiPageWikiLink Baylis–Hillman_reaction.
- Aldol_reaction wikiPageWikiLink Benzaldehyde.
- Aldol_reaction wikiPageWikiLink Biomimetics.
- Aldol_reaction wikiPageWikiLink Bisoxazoline_ligand.
- Aldol_reaction wikiPageWikiLink Bond_length.
- Aldol_reaction wikiPageWikiLink Boron.
- Aldol_reaction wikiPageWikiLink Boron_trifluoride.
- Aldol_reaction wikiPageWikiLink Branching_(polymer_chemistry).
- Aldol_reaction wikiPageWikiLink Cahn–Ingold–Prelog_priority_rules.
- Aldol_reaction wikiPageWikiLink Carbanion.
- Aldol_reaction wikiPageWikiLink Carbenium_ion.
- Aldol_reaction wikiPageWikiLink Carbohydrate.
- Aldol_reaction wikiPageWikiLink Carbonyl.
- Aldol_reaction wikiPageWikiLink Carbon–carbon_bond.
- Aldol_reaction wikiPageWikiLink Catalysis.
- Aldol_reaction wikiPageWikiLink Category:Addition_reactions.
- Aldol_reaction wikiPageWikiLink Category:Carbon-carbon_bond_forming_reactions.
- Aldol_reaction wikiPageWikiLink Charles-Adolphe_Wurtz.
- Aldol_reaction wikiPageWikiLink Chiral_auxiliary.
- Aldol_reaction wikiPageWikiLink Chiral_ligand.
- Aldol_reaction wikiPageWikiLink Chirality_(chemistry).
- Aldol_reaction wikiPageWikiLink Cis–trans_isomerism.
- Aldol_reaction wikiPageWikiLink Claisen_condensation.
- Aldol_reaction wikiPageWikiLink Computational_chemistry.
- Aldol_reaction wikiPageWikiLink Conformational_isomerism.
- Aldol_reaction wikiPageWikiLink Crystallization.
- Aldol_reaction wikiPageWikiLink Cyclohexane_conformation.
- Aldol_reaction wikiPageWikiLink David_A._Evans.
- Aldol_reaction wikiPageWikiLink Decarboxylation.
- Aldol_reaction wikiPageWikiLink Dehydration_reaction.
- Aldol_reaction wikiPageWikiLink Deprotonation.
- Aldol_reaction wikiPageWikiLink Diastereomer.
- Aldol_reaction wikiPageWikiLink Dibutylboron_trifluoromethanesulfonate.
- Aldol_reaction wikiPageWikiLink Diethyl_malonate.
- Aldol_reaction wikiPageWikiLink Dihydroxyacetone.
- Aldol_reaction wikiPageWikiLink Dimer_(chemistry).
- Aldol_reaction wikiPageWikiLink Discodermolide.
- Aldol_reaction wikiPageWikiLink E-Z_notation.
- Aldol_reaction wikiPageWikiLink E1cB-elimination_reaction.
- Aldol_reaction wikiPageWikiLink Electrophile.
- Aldol_reaction wikiPageWikiLink Enamine.
- Aldol_reaction wikiPageWikiLink Enantiomer.
- Aldol_reaction wikiPageWikiLink Enantioselective_synthesis.
- Aldol_reaction wikiPageWikiLink Enol.
- Aldol_reaction wikiPageWikiLink Epimer.
- Aldol_reaction wikiPageWikiLink Erythrose.
- Aldol_reaction wikiPageWikiLink Ester.
- Aldol_reaction wikiPageWikiLink Ether.
- Aldol_reaction wikiPageWikiLink Fructose_1,6-bisphosphate.
- Aldol_reaction wikiPageWikiLink Glucose.
- Aldol_reaction wikiPageWikiLink Glyceraldehyde_3-phosphate.
- Aldol_reaction wikiPageWikiLink Glycolysis.
- Aldol_reaction wikiPageWikiLink Glyoxylate_cycle.
- Aldol_reaction wikiPageWikiLink Glyoxylic_acid.
- Aldol_reaction wikiPageWikiLink Hajos–Parrish–Eder–Sauer–Wiechert_reaction.
- Aldol_reaction wikiPageWikiLink Hexamethylphosphoramide.
- Aldol_reaction wikiPageWikiLink Hexose.
- Aldol_reaction wikiPageWikiLink Howard_Zimmerman.
- Aldol_reaction wikiPageWikiLink Hydroxide.
- Aldol_reaction wikiPageWikiLink Imide.
- Aldol_reaction wikiPageWikiLink In_situ.
- Aldol_reaction wikiPageWikiLink Isocitrate_lyase.
- Aldol_reaction wikiPageWikiLink Isocitric_acid.
- Aldol_reaction wikiPageWikiLink Isotopic_labeling.
- Aldol_reaction wikiPageWikiLink Ivanov_reaction.
- Aldol_reaction wikiPageWikiLink Keto_acid.
- Aldol_reaction wikiPageWikiLink Ketone_enolate.
- Aldol_reaction wikiPageWikiLink Knoevenagel_condensation.
- Aldol_reaction wikiPageWikiLink Lactol.
- Aldol_reaction wikiPageWikiLink Lewis_acids_and_bases.
- Aldol_reaction wikiPageWikiLink Lithium.
- Aldol_reaction wikiPageWikiLink Lithium_diisopropylamide.
- Aldol_reaction wikiPageWikiLink Magnesium.