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Carbonyl Reductions

Even more highly selective ketone reductions are earned out with baker s yeast [61, 62] (equations 50 and 51) Chiral dihydronicotinamides give carbonyl reductions of high enantioselectivity [63] (equation 52), and a crown ether containing a chiral 1,4-dihydropyridine moiety is also effective [64] (equation 52). [Pg.309]

Reduction of unsaturated carbonyl compounds to the saturated carbonyl is achieved readily and in high yield. Over palladium the reduction will come to a near halt except under vigorous conditions (73). If an aryl carbonyl compound, or a vinylogous aryl carbonyl, such as in cinnamaldehyde is employed, some reduction of the carbonyl may occur as well. Carbonyl reduction can be diminished or stopped completely by addition of small amounts of potassium acetate (i5) to palladium catalysts. Other effective inhibitors are ferrous salts, such asferroussulfate, at a level of about one atom of iron per atom of palladium. The ferrous salt can be simply added to the hydrogenation solution (94). Homogeneous catalysts are not very effective in hydrogenation of unsaturated aldehydes because of the tendencies of these catalysts to promote decarbonylation. [Pg.40]

A variety of catalysts including copper, nickel, cobalt, and the platinum metals group have been used successfully in carbonyl reduction. Palladium, an excellent catalyst for hydrogenation of aromatic carbonyls is relatively ineffective for aliphatic carbonyls this latter group has a low strength of adsorption on palladium relative to other metals (72,91). Nonetheless, palladium can be used very well with aliphatic carbonyls with sufficient patience, as illustrated by the difficult-to-reduce vinylogous amide I to 2 (9). [Pg.66]

Carbonyl reduction begins to compete with olefin saturation when the double bond is hindered or the carbonyl is aromatic or an aromatic vinylog. In conjugated systems, deoxygenation may occur via an intermediate allylic alcohol (51). [Pg.70]

Cope rearrangement 17, 213 f., 643 Corey catalysts 74 f., 80 -, aldol condensations with 74 -, carbonyl allylations with 74 -, carbonyl reductions with 74 f. [Pg.791]

Cryogenic conditions (-78 °C) and an expensive reagent (L-Selectride ) to obtain high selectivity for carbonyl reduction in 5 Additional cost for cryogenic step... [Pg.244]

That molecule is then subjected to the standard carbonyl reduction, Birch reaction, oxidation, ethynylation and, finally, hydrolysis sequence (see 50 to 53). Hydrolysis of the enol ether under more strenuous conditions than was employed with 53 gives the conjugated ketone 65. The carbonyl group is then reduced to afford the corresponding 3p-alcohol (66). Exhaustive acetylation affords the potent oral progestin methynodiol diacetate (67). [Pg.149]

In respect of designing an economic production process, the stoichiometric cofactor required in carbonyl reductions or the respective oxidation reactions needs to be minimized that is, enabled by recycling of the cofactor. The measure for the efficiency of the recycling process is the total turnover number (TTN), which describes the moles of product synthesized in relation to the moles of cofactor needed. The different approaches in cofactor recycling were recently reviewed by Goldberg et at. [12]. [Pg.82]

Kaluzna, I.A., Matsuda, T., Sewell, A.K. and Stewart, J.D. (2004) Systematic investigation of Saccharomyces cerevisiae enzymes catalyzing carbonyl reductions. Journal of the American Chemical Society, 126 (40), 12827-12832. [Pg.163]

Scheme 43 In situ generation of allyl(hydrido)zirconocenes and their carbonyl reduction-allylation tandem processes. Scheme 43 In situ generation of allyl(hydrido)zirconocenes and their carbonyl reduction-allylation tandem processes.
The carbonyl reductases catalyze reduction of aldehydes and ketones by reduced pyridine nucleotides (NADH and/or NADPH). As mentioned earlier, alcohol dehydrogenase can perform this function in the presence of a high ratio of NADH to NAD+. Other enzymes capable of carbonyl reduction include the aldehyde and ketone reductases. The aldehyde and ketone reductases have a ubiquitous species distribution, with the enzymes present in organisms ranging from bacteria to vertebrates. The mammalian carbonyl reductases have been extensively reviewed (101). [Pg.352]

Figure 11.2 Catalysts and ligands for carbonyl reduction by borane. Figure 11.2 Catalysts and ligands for carbonyl reduction by borane.
Martin HJ, Breyer-Pfaff U, Wsol V, et al. Purification and characterization of akrlblO from human liver role in carbonyl reduction of xenobiotics. Drug Metab Dispos 2006 34(3) 464-470. [Pg.107]

Breyer-Pfaff U, Nill K. Carbonyl reduction of naltrexone and dolasetron by oxidoreductases isolated from human liver cytosol. J Pharm Pharmacol 2004 56(12) 1601—1606. [Pg.118]


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1,2-diols reductive coupling of carbonyl compounds

Alcohols by reduction of carbonyl compounds

Alcohols by reduction of carbonyl compounds with

Alcohols by reduction of carbonyls

Alcohols carbonyl compounds reduction

Alcohols carbonyl reductions

Alcohols from Carbonyl Compounds Reduction

Alcohols from Reduction of Carbonyl Compounds

Alcohols from alcohol reductive carbonylation

Alcohols from ester reductive carbonylation

Alkali metals carbonyl compound reduction

Alkenes from carbonyl compounds by reductive

Alkenes reductive coupling with carbonyl compounds

Alkyne-carbonyl reductive couplings

Aluminum carbonyl compound reductions

Aluminum carbonyl reduction

Aluminum, triethylhydride donor reduction of carbonyls

Ammonium formate carbonyl compound reduction

Application of hydrides as reductants for coordinated carbonyl ligands

Aromatic carbonyl groups, reduction

Asymmetric Carbonyl Reductions

Asymmetric reduction of carbonyl compounds

Biochemical reduction unsaturated carbonyl compounds

Borane carbonyl compound reduction

Borane, carbonyl reduction

Boranes, trifluorodiethyl ether complex carbonyl compound reduction

By Alan Cox 2 Reduction of the Carbonyl Group

By Reduction of Carbonyl Compounds

Carbonyl Additions and Reductions

Carbonyl Chemistry Organometallic Reagents Oxidation and Reduction

Carbonyl Reduction with

Carbonyl and Imine Reductions

Carbonyl catalytic reductive coupling

Carbonyl compounds Clemmensen reduction

Carbonyl compounds Wolff-Kishner reduction

Carbonyl compounds acid chlorides, reduction

Carbonyl compounds aliphatic, reduction

Carbonyl compounds aromatic, reduction

Carbonyl compounds asymmetric reduction

Carbonyl compounds enantiomeric reductions

Carbonyl compounds esters, reduction

Carbonyl compounds heteroaromatic, reduction

Carbonyl compounds hydride reduction

Carbonyl compounds metal hydride reduction

Carbonyl compounds reduction

Carbonyl compounds reduction by sodium borohydride

Carbonyl compounds reduction to enolates

Carbonyl compounds reduction, asymmetric induction

Carbonyl compounds reductions, zinc-acetic acid

Carbonyl compounds reductive alkylation

Carbonyl compounds reductive amination

Carbonyl compounds reductive coupling

Carbonyl compounds reductive coupling reactions

Carbonyl compounds reductive coupling with activated alkenes

Carbonyl compounds reductive deoxygenation

Carbonyl compounds, a-halo reduction

Carbonyl compounds, a-halo reductive cleavage

Carbonyl compounds, from nitro reductive amination

Carbonyl compounds, reductive

Carbonyl compounds, reductive etherification

Carbonyl derivatives reductions

Carbonyl group oxidation and reduction

Carbonyl group reduction

Carbonyl group selective reduction

Carbonyl group, reduction resonance structures

Carbonyl groups hydride reduction

Carbonyl groups stereoselective reductions

Carbonyl nickel-catalyzed reductive allylation

Carbonyl reductases reductions

Carbonyl reduction 486 Subject

Carbonyl reduction Lewis basic functional groups

Carbonyl reduction by the Cannizzaro reaction

Carbonyl reduction chiral compound stereoselective synthesis

Carbonyl reduction diastereoselective

Carbonyl reduction fragmentation reactions

Carbonyl reduction mechanism

Carbonyl reduction of P-keto acetals

Carbonyl reduction proton donors

Carbonyl reduction under Meerwein-Ponndorf-Verley conditions

Carbonyl reduction using borohydrides

Carbonyl reduction using other methods

Carbonyl tosylhydrazone reductive deoxygenation

Carbonyl ylide reduction reaction

Carbonylation reductive, alcohols

Carbonylative reductive elimination

Catalysts carbonyl compound reduction

Catalysts reductive carbonylation

Catalytic reductive carbonylation

Catalytic reductive carbonylation nitrobenzenes

Chemoselective carbonyl group reduction

Conjugated carbonyl compounds, reduction with

Coupling reductive carbonyl

Cyclohexene carbonyl compound reduction

Deuterium labelling carbonyl reduction

Diastereoselective reduction of carbonyls

Dimethyl carbonate reductive carbonylation

Electrochemical reduction carbonyl compounds

Electrochemical reductive cleavage a-oxygenated carbonyl compounds

Electrophiles carbonyl compounds reduction

Enantioselective Carbonyl Reductions

Enantioselective Reduction of Carbonyl Compounds

Enantioselective reactions carbonyl reductions

Enantioselectivity reduction, of carbonyl compounds

Enzymatic Asymmetric Reduction of Carbonyl Compounds

Enzymic Asymmetric Carbonyl Reductions

Esters reductive carbonylation

Grignard reagents carbonyl reduction

High-nuclearity carbonyl clusters reduction reactions

Hydride Reduction of a Carbonyl Group

Hydride carbonyl reduction

Hydride donors reduction of carbonyls

Hydride reagents carbonyl compound reduction

Hydride reduction of carbonyl

Hydrocarbons from carbonyl compound reduction

Hydrogenation carbonyl compound reduction

Hydroxy carbonyls, reduction

Introduction to Carbonyl Chemistry Organometallic Reagents Oxidation and Reduction

Ionic carbonyl compound reduction

Iron carbonyl complexes reduction reactions

Iron carbonyls reductive cleavage

Labelling carbonyl reduction

Lactam carbonyl selective reduction

Lewis acids carbonyl compound reduction

Lewis bases carbonyl reductions

Limonene carbonyl compound reduction

Lithium aluminum hydride reduction, alcohols from, with carbonyl compounds

Lithium aluminum hydride, reduction carbonyls

Lithium carbonyl compound reduction

Metal carbonyls borohydride reduction

Metal carbonyls reduction

Metal carbonyls reductive carbonylation

Metal carbonyls reductive elimination

Metal groups carbonylates, reductive elimination reactions

Methyl esters, reductive carbonylation

Methyl ketals, reductive carbonylation

Nickel carbonyl, reduction

Nitro reductive carbonylation

Nitroarenes reductive carbonylation

One-Electron Reductions of Carbonyl Compounds and Esters Reductive Coupling

Organic carbonyl compounds, reductive

Organic carbonyl compounds, reductive amination

Osmium carbonyl clusters reduction

Oxidation and Reduction of Carbonyl Compounds

Oxidation-reduction reactions, carbonyl compounds

Palladium reductive carbonylation

Pre-Reduction of Carbonyl Groups with Lithium Aluminum Hydride

Preparation by Reduction of Carbonyl Compounds

Propylene reductive carbonylation

Reactions at the Carbonyl Group—Oxidation and Reduction

Reduction a-substituted carbonyl compounds

Reduction carbonyl methylenation step

Reduction carbonyl, borohydride

Reduction carbonylation

Reduction carbonylation

Reduction in carbonylation

Reduction of Aldehyde and Ketone Carbonyls

Reduction of Carbonyl Compounds to Alkenes

Reduction of Carbonyl Compounds to Hydrocarbons

Reduction of Carbonyl Compounds with Aluminum Alkoxides

Reduction of Carbonyl Derivatives

Reduction of Carbonyl and Other Functional Groups

Reduction of Functionalized Carbonyl and Dicarbonyl Compounds

Reduction of Labeled Prochiral Carbonyl Compounds and Oximes

Reduction of Main Group Oxides via Metal Carbonyls and Carbonylate Anions

Reduction of Metal Carbonyls with Alkali Metals and Sodium Tetrahydridoborate in Liquid Ammonia

Reduction of Other Carbonyl Compounds

Reduction of a, 3-unsaturated carbonyl

Reduction of a,/?-unsaturated carbonyl compounds

Reduction of a-Hydroxyimino Carbonyl Compounds

Reduction of activated carbonyl groups

Reduction of carbonyl and nitro functionalities

Reduction of carbonyl compounds

Reduction of carbonyl functionalities

Reduction of carbonyl functions

Reduction of carbonyl groups

Reduction of carbonyls

Reduction of o-B-unsaturated carbonyl compounds

Reduction of the carbonyl group

Reduction of unsaturated carbonyl compounds

Reduction reaction carbonyls

Reduction reactions carbonyl compounds

Reduction unsaturated carbonyl compounds

Reduction, azobenzenes carbonyl compounds

Reduction, induced carbonyl substitution

Reductions of Carbonyl Compounds to Alcohols

Reductions of metal carbonyls

Reductive Alkylation of Ammonia with Carbonyl Compounds

Reductive Alkylation of Primary Amines with Carbonyl Compounds

Reductive Carbonylation of Mixed Metal Complexes

Reductive Coupling of Carbonyl-Containing Compounds and Imines Using Reactive Manganese

Reductive Coupling of Carbonyls to Alkenes Adamantylideneadamantane

Reductive Deoxygenation of Carbonyl Groups

Reductive Deoxygenation of Carbonyl Groups to Methylene

Reductive N-Alkylation of Primary Amides with Carbonyl Compounds

Reductive amination of carbonyl compounds

Reductive amination of carbonyls

Reductive amination of fluoro-carbonyl compounds

Reductive carbonylation

Reductive carbonylation examples

Reductive carbonylation mechanism

Reductive carbonylation methanol

Reductive carbonylation methyl acetate

Reductive carbonylation thiocarbonylation reactions

Reductive carbonylations

Reductive coupling of carbonyl compounds

Reductive coupling of carbonyls to alkenes

Reductive coupling reactions carbonyl olefination

Reductive dimerization of carbonyl compounds

Reductive dimerization, of carbonyl

Reductive enzymes carbonyl reductases

Reductive of carbonyl compounds

Reductive reactions carbonyl reductases

Reductive reactions carbonylation

Regioselectivity carbonyl reduction

Selective reduction of carbonyl group in

Selectivity in the Reduction of Carbonyl Derivatives Containing a Chiral Carbon

Sodium borohydride carbonyl compound reduction

Sodium borohydride, reduction of carbonyl

Sodium borohydride, reduction of carbonyl compounds

Sodium carbonyl compound reduction

Sodium imide carbonyl reduction with

Solvation carbonyl reduction

Stereochemistry of carbonyl reduction

Stereoselective Carbonyl Reductions

Stereoselective reductions, of carbonyl

Stereoselective reductions, of carbonyl groups

Subject reductive carbonylation

Synthesis reductive carbonylation

Terminology for Reduction of Carbonyl Compounds

The Role of Proximal, Lewis Basic Functional Groups in Carbonyl Reduction

The Stereochemistry of Carbonyl Reduction

Topic 2.4. Polar Substituent Effects in Reduction of Carbonyl Compounds

Zinc, dialkylhydride donor reduction of carbonyls

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