ChemInform Abstract: New Families of Enantiopure Cyclohexenone cis‐Diol, o‐Quinol Dimer and Hydrate Metabolites from Dioxygenase‐Catalyzed Dihydroxylation of Phenols.
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.Keywords:
Dihydroxylation
Enantiopure drug
Cyclohexenone
The preparation of 5-substituted 2,3-methanopyrrolidines by the stereoselective cyclization of zincated α-amino nitriles derived from enantiopure α-branched homoallylamines has been investigated. The formation of trans adducts in excellent diastereoselectivities (up to >98:2) and good yields (up to 71%) is observed. The absolute configuration and enantiomeric excess are dependent on the nitrogen protecting group.
Enantiopure drug
Enantiomeric excess
Absolute Configuration
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Synthesis of novel polyhydroxylated derivatives of decalin is described. The presented methodology consists in a one-pot copper-catalyzed 1,4-addition of vinylmagnesium bromide to sugar-derived cyclohexenone, followed by an aldol reaction with a derivative of but-3-enal. The obtained diene is then subjected to an assisted tandem catalytic sequence: ring-closing metathesis with the subsequent reuse of the Ru-catalyst in the syn -dihydroxylation. The stereochemical outcome of these reactions is discussed.
Dihydroxylation
Aldol reaction
Decalin
Cyclohexenone
Ring-Closing Metathesis
Cascade reaction
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The importance for the right order of functional group introduction and manipulation (good timing) was demonstrated in the course of a total synthesis of phoslactomycin A. The synthetic strategy comprised a Cu(I)-thiophene carboxylate (CuTC, Liebeskind's reagent)-mediated coupling to introduce the Z,Z-diene at the final stage of the synthesis in the presence of a protected phosphate. Key features for the assembly of the C1-C13 fragment were an asymmetric dihydroxylation, an Evans-aldol reaction and an advanced protective group strategy. The C14-C21 fragment was accessible via an asymmetric 1,2-addition to cyclohexenone and a subsequent diastereoselective ketone reduction. One crucial task was the dihydroxylation of the C8-C9 alkene, the introduction of the C6-C7 double bond and the generation of the C25-nitrogen functionality. A second example consisted of the best sequence for the generation of the functional groups in the core part (first phosphorylation, second iodo-olefination, third azide/carbamate conversion). The synthetic solutions from this approach are compared with the already existing contributions in the phoslactomycin area.
Dihydroxylation
Alkene
Functional group
Cyclohexenone
Protecting group
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Abstract For Abstract see ChemInform Abstract in Full Text.
Enantiopure drug
Kinetic resolution
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Abstract The enantiopure oxazolines are synthesized without using any catalysts and solvents from various nitriles and enantiopure amino alcohols under microwave irradiation at high temperature (150 to 240 °C) in short reaction time (60 to 100 min).
Enantiopure drug
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Enantiopure drug
Dihydroxylation
Vicinal
Stereospecificity
Kinetic resolution
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Enantiopure drug
Dihydroxylation
Acrolein
Glyceraldehyde
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Abstract A new route to enantiopure dihydropyridines of type (VI) and (XIII) is reported.
Enantiopure drug
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Abstract A RuPHOX−Ru catalyzed asymmetric hydrogenation of γ‐keto acids has been developed, affording the corresponding enantiopure γ‐lactones in high yields and with up to 97% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 10000 S/C) under the indicated reaction conditions and the resulting products can be transformed to several enantiopure building blocks, biologically active compounds and enantiopure drugs. magnified image
Enantiopure drug
Asymmetric hydrogenation
Reaction conditions
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Abstract Chiral butyrolacto[3,4‐ b ]‐2(S)‐6( R )‐l‐N‐alkylaziridines 7 were synthesized in enantiopure form utilizing racemic 5‐methoxy‐3‐bromo‐2(5 H )furanone (5) and available amines (6) as key precursors. After highly effective reduction of 7, the functionalized 2( S ),3( R )‐dihydroxymethyl‐ N ‐alkylaziridines (8) were obtained in good yields with ≥98% ee . This is a simple and practical method for the preparation of enantiopure aziridines which are important intermediates in the synthesis of biologic active molecules.
Enantiopure drug
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