ChemInform Abstract: Chiral Pyridin‐3‐ones and Pyridines: Syntheses of Enantiopure 2,4‐Disubstituted 6‐Hydroxy‐1,6‐dihydro‐2H‐pyridin‐3‐ones, 2,3‐Disubstituted 4‐Iodopyridines, and Enantiopure 2,3‐Disubstituted 4‐Pyridinemethanols.
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Abstract A new route to enantiopure dihydropyridines of type (VI) and (XIII) is reported.Keywords:
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The authors recently reported the synthesis of enantiopure trans-ethynylaziridines by the stereoselective addition of racemic allenylzinc to enantiopure N-tert-butanesulfinimines. In this paper they discovered that the addition of 60 equivalents of HMPA to the reaction reversed the stereoselection to give predominantly cis-ethynylaziridines.
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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.
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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).
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The enantiopure iron complex 4 reacts under the influence of BF3·OEt2 with allylsilanes and enol acetates through a cationic intermediate in which the chirality of 4 is preserved, yielding enantiopure 5-substituted 3-pyrrolin-2-ones.
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Abstract An enantiopure syn-benzocyclotrimer 1 was selectively synthesized from an enantiopure halonorbornene 2 through regio-selective cyclotrimerization catalyzed by palladium nanoclusters. The yield of 1 was dependent on the stability of the palladium clusters, which was ascertained from the appearance and TEM images of the reaction mixtures. The thus-prepared enantiopure benzocyclotrimer will serve as a key intermediate for the synthesis of C3v symmetric chiral buckybowls.
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Abstract The synthesis of enantiopure molecules from achiral precursors without the need for pre-existing chirality is a major challenge associated with the origin of life. We here show that an enantiopure product can be obtained from achiral starting materials in a single organic reaction. An essential characteristic of this reaction is that the chiral product precipitates from the solution, introducing a crystal–solution interface which functions as an asymmetric autocatalytic system that provides sufficient chiral amplification to reach an enantiopure end state. This approach not only provides more insight into the origin of life but also offers a pathway to acquire enantiopure compounds for industrial applications.
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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.
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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
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