Organic chemistry articles within Nature Chemistry

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  • Article |

    Covalent organic frameworks (COFs) organize organic subunits into predictable and precise networks with long-range order. The limited generality of methods for COF synthesis has thus far precluded the incorporation of complex building blocks into these emerging materials. Now, a new Lewis acid-catalysed protocol for boronic ester formation provides a two-dimensional COF containing stacked phthalocyanine chromophores.

    • Eric L. Spitler
    •  & William R. Dichtel

  • Article |

    The development of benign methods for carbon–carbon bond formation is a continuing challenge. Here, a simple procedure for the hydroacylation of α,β-unsaturated esters is described, in which auto-oxidation of aldehydes and subsequent acyl radical addition to α,β-unsaturated esters occurs without the need for additional reagents.

    • Vijay Chudasama
    • , Richard J. Fitzmaurice
    •  & Stephen Caddick

  • Article |

    Thermal reduction of graphene oxide is an attractive route towards the preparation of graphene, but complete removal of residual oxygen is problematic. Now, molecular dynamics simulations elucidate the chemical changes involved in this process.

    • Akbar Bagri
    • , Cecilia Mattevi
    •  & Vivek B. Shenoy

  • News & Views |

    Ultrasound can be used to control molecular processes as delicate as rotation around a single carbon–carbon bond.

    • S. Karthikeyan
    •  & Rint P. Sijbesma

  • Article |

    A convergent route to stereodefined skipped polyenes, which proceeds through the direct union of vinylcyclopropanes with alkynes, is described. Overall, C?C bond formation occurs in concert with the establishment of up to three stereodefined alkenes, through a tandem stereoselective metallacycle-mediated coupling/stereospecific fragmentation sequence.

    • Todd K. Macklin
    •  & Glenn C. Micalizio

  • Article |

    The difficulty in the stereoselective introduction of 1,2-cis-glycosides is a major stumbling block in the solid-supported synthesis of oligosaccharides. Now, this has been achieved for a biologically important glucoside containing multiple 1,2-cis-glycosidic linkages with complete anomeric control by using glycosyl donors having a participating (S)-(phenylthiomethyl)benzyl chiral auxiliary at C-2.

    • Thomas J. Boltje
    • , Jin-Hwan Kim
    •  & Geert-Jan Boons

  • Research Highlights |

    Metal–organic cages made with 1,1-biphenyl ligands act as hosts for enantioselective absorption.

    • Neil Withers

  • Research Highlights |

    A combined theoretical and experimental approach has been used to improve catalysts for the selective oxidation of carbon monoxide in hydrogen feedstocks.

    • Gavin Armstrong

  • News & Views |

    The composition of dynamic small-molecule libraries can be biased by the addition of a target compound — such as a protein — that binds selectively to one of the components in the mixture. The chemistry of the library must, however, be compatible with the target and it has now been shown that aniline-catalysed exchange of acylhydrazones fits the bill.

    • Benjamin L. Miller

  • Article |

    A kinetic and thermodynamic analysis of the ruthenium-catalysed ring-closing metathesis reaction has been achieved through the study of key intermediates accessible, for the first time, from 14-electron phosphonium alkylidene catalyst precursors. High intrinsic activities and a thermodynamic preference for ring-closing versus ring-opening reactions is observed.

    • Edwin F. van der Eide
    •  & Warren E. Piers

  • Article |

    Iron is an abundant, low cost and environmentally benign metal. Here, iron complexes are shown to be the most effective catalysts for asymmetric O–H insertion reactions. These results should encourage the use of iron, rather than more traditional precious metals, in the development of greener organometallic catalysts for asymmetric transformations.

    • Shou-Fei Zhu
    • , Yan Cai
    •  & Qi-Lin Zhou

  • Article |

    The ability to selectively transform the C–H bonds of simple alkanes to useful functional groups such as alcohols is a key step in the move away from petrochemical feedstocks. Now, it has been shown that the oxidation of alkanes can be catalysed by a bulky polyoxometalate species using hydrogen peroxide as a stoichiometric oxidant.

    • Keigo Kamata
    • , Kazuhiro Yonehara
    •  & Noritaka Mizuno

  • Article |

    Helical molecules in biological systems commonly undergo extension, contraction and unidirectional twisting motions, but such twisting — promising for the construction of molecular machines — has rarely been achieved in synthetic systems. Now, a chiral double helix has been prepared whose spring-like motion is accompanied by an anisotropic twist under the control of sodium ions.

    • Kazuhiro Miwa
    • , Yoshio Furusho
    •  & Eiji Yashima

  • News & Views |

    Molecular 'boxes' can hold other molecules and often serve as the moving parts in molecular switches. The latest addition to this class of compounds is a simple-to-prepare positively charged macrocycle that can encircle molecular guests of appropriate size and charge — and offers new opportunities for assembling stimuli-responsive structures.

    • Andrew I. Share
    •  & Amar H. Flood

  • Research Highlights |

    Two different but successful approaches to the synthesis of (+)-complanadine A will help in investigations of its interesting biological activity.

    • Stephen Davey

  • Review Article |

    The synthesis or separation of chiral compounds is crucial for many areas of chemistry, with chiral solids having important roles as catalysts or separating agents. This Review covers recent progress and future avenues for developing methods of preparing chiral solids from achiral starting materials.

    • Russell E. Morris
    •  & Xianhui Bu

  • Research Highlights |

    A rationally designed highly electrophilic iridium complex excels at catalysing the formation of five-membered carbocycles.

    • Stephen Davey

  • Research Highlights |

    A double-reductive alkylation of amides with two different organometallic compounds allows the direct formation of a tertiary alkylamines in one pot.

    • Stephen Davey

  • Research Highlights |

    An efficient heterogeneous catalyst for the conversion of glucose into fructose has been prepared by incorporating tin centres into the framework of a zeolite.

    • Anne Pichon

  • News & Views |

    The convergent total synthesis of the pore-forming polytheonamide B — a linear peptide natural product — pokes holes through perceived limitations in de novo peptide synthesis, and provides access to novel synthetic membrane channels.

    • Craig J. Forsyth

  • News & Views |

    A strong acid catalyst and a small change to one reactant have transformed a 37-year-old 'curiosity' into a useful chemical reaction that has great potential in organic synthesis.

    • Sarah E. Steinhardt
    •  & Christopher D. Vanderwal

  • Article |

    Macrocyles capable of hosting other molecules inside their hollow interiors have been used extensively to make threaded complexes and interlocked molecules. Now, a relatively large and flexible tetracationic macrocycle has been shown to bind anionic guests to form pseudorotaxanes that form extended structures in solution and the solid state.

    • Han-Yuan Gong
    • , Brett M. Rambo
    •  & Jonathan L. Sessler

  • Research Highlights |

    The intercalation of potassium into a simple aromatic hydrocarbon results in a new class of organic superconductors.

    • Neil Withers

  • Article |

    Chiral thiols and organosulfur compounds are important in many areas of chemistry but there are relatively few methods available for their efficient enantioselective synthesis. Here, a kinetic resolution of chiral thiols is reported along with a demonstration that a concomitant desymmetrization of the acylating agent is beneficial for the selectivity of both processes.

    • Aldo Peschiulli
    • , Barbara Procuranti
    •  & Stephen J. Connon

  • Research Highlights |

    Thermally stable stereoisomers can be interconverted by the application of a mechanical force using ultrasound irradiation.

    • Stephen Davey

  • News & Views |

    The long-awaited first total synthesis of the structurally intriguing natural product palau'amine has now been achieved. The synthesis features cascade reactions and an 'across ring' stitching of a 'macropalau'amine', and sets the bar for future efforts towards an enantioselective variant.

    • Daniel Romo

  • News & Views |

    Electromerism is an unfamiliar concept to many chemists and refers to molecules that are not conventional isomers but instead differ in how the electrons are distributed across their structure. A novel example of such electromers has now been demonstrated.

    • Thomas Bally

  • Article |

    Steric, torsion, stereoelectronic and polar effects are widely used to explain and predict the stereochemical outcome of synthetic organic reactions. Here, the asymmetric distortion of the reactant is considered and used to explain the observed stereoselectivity where these accepted models are unable to provide a clear prediction.

    • Robert V. Kolakowski
    •  & Lawrence J. Williams

  • Article |

    Stepwise deuteration of protonated methane CH5+ — a fluxional structure that undergoes ‘hydrogen scrambling’ — leads to dramatic changes in the infrared spectra of the isotopologues. The spectra can be assigned using ab initio quantum simulations that account for the non-classical occupation — by H and D atoms — of topologically different sites within the molecule.

    • Sergei D. Ivanov
    • , Oskar Asvany
    •  & Stephan Schlemmer

  • Article |

    A triflimide-catalysed rearrangement of N-allylhydrazones has been developed that allows for the generation of a sigma bond between two unfunctionalized sp3 carbons such that no clear marker remains for how the bond was formed. This traceless bond construction offers new avenues for convergent fragment coupling in synthetic strategies.

    • Devon A. Mundal
    • , Christopher T. Avetta Jr
    •  & Regan J. Thomson

  • Article |

    Polytheonamide B is a large non-ribosomal peptide with very high bioactivity. The synthesis described here includes the first preparation of several non-proteinogenic amino acids and a general coupling strategy for large non-natural peptides. The synthesis is a key step necessary to understand and utilize the bioactivity of this and similar compounds.

    • Masayuki Inoue
    • , Naoki Shinohara
    •  & Shigeru Matsuoka

  • Review Article |

    The field of organocatalysis has grown rapidly in the past decade to become, along with metal catalysis and biocatalysis, a third pillar of asymmetric catalysis. Here, progress in the use of organocatalytic cascade reactions for total synthesis is reviewed. The elegance and efficiency of such cascades mean that they have emerged as a powerful tool in synthetic organic chemistry.

    • Christoph Grondal
    • , Matthieu Jeanty
    •  & Dieter Enders

  • Article |

    The uptake of ammonia by a covalent–organic framework (COF) containing a high density of Lewis-acidic boron sites has been found to be significantly greater than that exhibited by other state-of-the-art porous materials. The ammonia can be removed by heating under vacuum and the structural integrity of the COF is maintained during adsorption/desorption cycles.

    • Christian J. Doonan
    • , David J. Tranchemontagne
    •  & Omar M. Yaghi

  • Article |

    The synthesis of interlocked compounds such as catenanes and rotaxanes has undergone much development in recent years, but molecular knots are still relatively hard to make. It has now been shown that a linear bipyridine oligomer can fold around a single zinc-ion template to form a complex that can be cyclized to give a molecular trefoil knot.

    • Jun Guo
    • , Paul C. Mayers
    •  & Christopher A. Hunter

  • News & Views |

    The stereochemical lability of cycloalkylzinc reagents combined with a large difference in reactivity between epimers has been exploited to form a wide variety of interesting organic compounds with both high yields and diastereoselectivities.

    • Frank Glorius

  • News & Views |

    A molecular 'walker' can be made to move up and down a molecular 'track' by alternately locking and unlocking the two different types of covalent bonds that join the two components together. By changing the conditions under which one of the bond-forming/bond-breaking processes occurs, a directional bias for walking can be achieved.

    • Sijbren Otto

  • Article |

    The selective construction of multiple adjacent stereocentres is an important challenge for synthetic organic methodology, and only a handful of catalytic methods exist that can forge adjacent quaternary and tertiary stereocentres. Here, a palladium-catalysed multiple-bond-forming cascade leads to the construction of such systems in high yield, diastereomeric ratio and enantiomeric excess.

    • Jan Streuff
    • , David E. White
    •  & Brian M. Stoltz

  • Article |

    Highly diastereoselective Negishi cross-coupling reactions between 2-, 3- and 4-substituted cycloalkylzinc reagents and aryl iodides are described. In all cases, the thermodynamically most stable diastereomers of the cross-coupling products were obtained. NMR spectroscopy and density functional theory calculations were performed in order to rationalize the observed stereoselectivities.

    • Tobias Thaler
    • , Benjamin Haag
    •  & Paul Knochel

  • Article |

    The bulk properties of materials that lack long-range order have been widely studied, but their local structures remain difficult to elucidate. Now, using scanning tunnelling microscopy, researchers have been able to look more closely at the structural motifs of robust, two-dimensional glassy networks assembled through metal–ligand interactions.

    • Matthias Marschall
    • , Joachim Reichert
    •  & Johannes V. Barth

  • News & Views |

    Among the wide variety of synthetic processes that chemists have developed, only a few can be carried out under physiological conditions. A condensation reaction that is controlled by the constituents of cells has led to the formation of nanostructures within living cells.

    • Bing Xu

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