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Carbonyl allylation information


In organic chemistry, carbonyl allylation describes methods for adding an allyl anion to an aldehyde or ketone to produce a homoallylic alcohol.[1] The carbonyl allylation was first reported in 1876 by Alexander Zaitsev and employed an allylzinc reagent.[2]

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  1. ^ Yus, Miguel; González-Gómez, José C.; Foubelo, Francisco (2011). "Catalytic Enantioselective Allylation of Carbonyl Compounds and Imines". Chemical Reviews. 111 (12): 7774–7854. doi:10.1021/cr1004474. PMID 21923136.
  2. ^ Michael; Saytzeff, Alexander (1877). "Synthese des Allyldimethylcarbinols". Justus Liebigs Annalen der Chemie. 185 (2–3): 151–169. doi:10.1002/jlac.18771850204. ISSN 1099-0690.

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Carbonyl allylation

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carbonyl allylation describes methods for adding an allyl anion to an aldehyde or ketone to produce a homoallylic alcohol. The carbonyl allylation was...

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Krische allylation

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carbonyl allylations are frequently applied to the synthesis of polyketide natural products. In 1978, Hoffmann reported the first asymmetric carbonyl...

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Allyl group

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include carbonyl allylation with allylmetallic reagents, such as allyltrimethylsilane, or the iridium-catalyzed Krische allylation. Allylation can be effected...

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Organostannane addition

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cases, a ketone. The reaction is widely used for carbonyl allylation. Organostannane addition to carbonyl groups constitutes one of the most common and efficient...

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Organoindium chemistry

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regioselectivity of allylation mediated by indium in water is dependent on the steric effects of the substituents on both the intermediate and carbonyl. An α-attack...

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Protecting group

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carbonyl groups, and cannot be discouraged by any means. When an ester must be reduced in the presence of a carbonyl, hydride attack on the carbonyl must...

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Decarboxylation

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J.; Tunge, J. A. (2011). "Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions". Chem. Rev. 111 (3): 1846–1913. doi:10.1021/cr1002744...

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Asymmetric induction

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[clarification needed] Several models exist to describe chiral induction at carbonyl carbons during nucleophilic additions. These models are based on a combination...

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Grignard reaction

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vinyl, or aryl magnesium halides (Grignard reagent) are added to the carbonyl groups of either an aldehyde or ketone under anhydrous conditions. This...

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Borylation

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4-diols and anti-diols. This kind of reaction is known as Rouch asymmetric allylation. In 2011, R. A. Fernandes and P. Kattanguru have completed an improved...

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Group 2 organometallic chemistry

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organic synthesis: unprecedented .alpha.-selective and stereospecific allylation of carbonyl compounds". Journal of the American Chemical Society. 113 (23):...

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Keck asymmetric allylation

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In organic chemistry, the Keck asymmetric allylation is a chemical reaction that involves the nucleophilic addition of an allyl group to an aldehyde. The...

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Organotantalum chemistry

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organotantalum reagents promote the conjugate allylation of enones. Although the direct allylation of carbonyl groups is prevalent throughout the literature...

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Organozinc chemistry

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useful coupling partners. This group transfer reaction can be used in allylation, or other coupling reactions (such as Negishi coupling). One of the major...

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Sakurai reaction

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beta-silyl carbocationic intermediate, the beta-silicon effect. Allylation of a carbonyl ketone (compound containing a ketone group and two different functional...

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Sigmatropic reaction

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adaptation of the Claisen rearrangement and effectively a decarboxylative allylation. The Fischer indole synthesis is a chemical reaction that produces the...

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Organoiron chemistry

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iron carbonyls are the three neutral binary carbonyls, iron pentacarbonyl, diiron nonacarbonyl, and triiron dodecacarbonyl. One or more carbonyl ligands...

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Organogallium chemistry

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para-xylene. : A specific niche indium research topic is indium mediated allylation. C. Elschenbroich, A. Salzer Organometallics : A Concise Introduction...

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Barbier reaction

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organometallic reaction between an alkyl halide (chloride, bromide, iodide), a carbonyl group and a metal. The reaction can be performed using magnesium, aluminium...

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List of organic reactions

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Hydroboration Hydrocarbon cracking Hydrohalogenation Indium mediated allylation Ing–Manske procedure Ipso substitution Ireland–Claisen rearrangement Isay...

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Barium iodide

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Yamamoto, H.; Allylbarium Reagents: Unprecedented Regio- and Stereoselective Allylation Reactions of Carbonyl Compounds. J. Am. Chem. Soc.1994, 116,6130-6141...

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Carvone

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using propan-2-ol and aluminium isopropoxide effects reduction of the carbonyl group only to provide carveol (5); a combination of sodium borohydride...

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Methylation

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Matsushita, Hajime (1984). "Palladium-Catalyzed Synthesis of 1,4-Dienes by Allylation of Alkenyalane: α-Farnesene". Organic Syntheses. 62: 31. doi:10.15227/orgsyn...

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Diallyl carbonate

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as an acrylate agent. Allyl carbonates are widely used in Tsuji-Trost allylation, promoting the formation of carbanions, boronates, phosphides, amides...

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