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Synthesis of 5-Amino and 3,5-Diamino Substituted 1,2,4-Thiadiazoles by I2-Mediated Oxidative N–S Bond Formation
10.1021/acs.joc.7b00814 2017-05-12 An oxidative N–S bond formation reaction has been established for 1,2,4-thiadiazole synthesis employing molecular iodine as the sole oxidant. The features of the present reaction include no use of transition metals, mild reaction conditions, simple operation,... |
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The Synthesis of Chiral β,β-Diaryl Allylic Alcohols and Their Use in the Preparation of α-Tertiary Allylamines and Quaternary α-Amino Acids
10.1021/acs.joc.7b00475 2017-05-11 An approach to nonracemic β,β-diarylsubstituted allyl alcohols is described. Their synthesis starts from l-lactic acid-derived propargyl alcohol, which is submitted to sequential Sonogashira/Suzuki or Sonagashira/Stille coupling reactions. Both approaches ena... |
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Total Synthesis of γ-Indomycinone and Kidamycinone by Means of Two Regioselective Diels–Alder Reactions
10.1021/acs.joc.7b00544 2017-05-11 An efficient access for the synthesis of pluramycinones is described. Total syntheses of racemic γ-indomycinone and kidamycinone were achieved by means of two Diels–Alder reactions. A first Diels–Alder condensation followed by a Stille cross-coupling is used ... |
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Unexpected Observation of the Dimroth Rearrangement in the Ribosylation of 4-Aminopyrimidines
10.1021/acs.joc.7b00780 2017-05-11 A method for the preparation of 1-(N-ribofuranosyl)-6-imino-1,6-dihydropyrimidin-4-amines 3 or 4-(N-ribofuranosyl)-6-aminopyrimidines 4 via glycosylation of 4-aminopyrimidines 2 or 5 is described. Silylated 4-aminopyrimidines 2 or 5 upon ribosylation with 1 p... |
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Theoretical Study of the BF3-Promoted Rearrangement of Oxiranyl N-Methyliminodiacetic Acid Boronates
10.1021/acs.joc.7b01096 2017-05-11 The mechanism of the rearrangement of oxiranyl N-methyliminodiacetyl (MIDA) boronates in dicholoromethane has been extensively investigated with density functional theory. Several reaction pathways were examined. Our results revealed that the most-favorable m... |
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Impact of Conjugation and Hyperconjugation on the Radical Stability of Allylic and Benzylic Systems: A Theoretical Study
10.1021/acs.joc.7b00549 2017-05-11 Resonantly stabilized radicals are some of the most investigated chemical species due to their preferential formation in a wide variety of chemical environments. Density functional theory and post-Hartree–Fock calculations were utilized to elucidate the chemi... |
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Copper-Catalyzed Functionalizations of C60 with Amino Alcohols
10.1021/acs.joc.7b00741 2017-05-11 CuI-catalyzed diverse functionalizations of C60 with amino alcohols with aerobic oxygen as the sole oxidant have been explored. For 2-/3-amino alcohols, an aminooxygenation reaction occurs to generate fulleromorpholine and fullerooxazepane derivatives. When a... |
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Chemoselective Reduction of Azlactones Using Schwartz’s Reagent
10.1021/acs.joc.7b00820 2017-05-11 Highly chemoselective addition of Schwartz’s reagent to widely available azlactones is described. This method allows the preparation of challenged functionalized α-amino aldehydes, in good to high isolated yields at room temperature, after only 2 min reaction... |
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Synthesis of 4-Halo-3(2H)-furanones Using Intramolecular Cyclization of Sulfonium Salts
10.1021/acs.joc.7b00399 2017-05-11 A simple and efficient synthesis of 4-halo-3(2H)-furanones by halogenative intramolecular cyclization of sulfonium salts is described, which can expedite the production of a variety of 4-bromo- or 4-iodo-3(2H)-furanones, useful synthetic building blocks, in g... |
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Svetamycins A–G, Unusual Piperazic Acid-Containing Peptides from Streptomyces sp.
10.1021/acs.joc.7b00228 2017-05-10 Seven new halogenated peptides termed svetamycins A–G (1–7) have been isolated from laboratory cultures of a Streptomyces sp. Svetamycins A–D, F, and G are cyclic depsipeptides, whereas svetamycin E is a linear analogue of svetamycin C. Their structures were ... |