Stereochemistry

Stereochemistry is the scientific concept that describes the relationship between chemical compounds which have the same molecular formula and identical functional groups but with different three dimensional arrangements of atoms. These molecules are known as stereoisomers and can have very different properties from one another, particularly when interacting with biological systems.

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Latest Research and Reviews

  • Research | | open

    Confined environments may have a significant influence on the transition state and, consequently, on the stereochemical outcome of a chemical reaction. Here, the authors show a droplet size-dependent chirality amplification effect for two model reactions in confined organic droplets surrounded by water cages.

    • Choong Eui Song
    • , Si Joon Park
    • , In-Soo Hwang
    • , Min Jung Jung
    • , So Young Shim
    • , Han Yong Bae
    •  & Ji Yoon Jung
  • Research | | open

    Cis-trans lactam amide rotation is a fundamental process and its understanding might aid molecular design. Here, the authors report the synthesis and study of bicyclic lactams which undergo spin through 360 degrees as in open-chain amides, due to the occurrence of nitrogen pyramidalization.

    • Yuko Otani
    • , Xin Liu
    • , Hisashi Ohno
    • , Siyuan Wang
    • , Luhan Zhai
    • , Aoze Su
    • , Masatoshi Kawahata
    • , Kentaro Yamaguchi
    •  & Tomohiko Ohwada
  • Research |

    Despite their huge potential in medicinal chemistry, current approaches for the synthesis of fluorinated piperidines are often impractical. A straightforward process for the rhodium-catalysed dearomatization–hydrogenation of fluoropyridines has now been described. This strategy enables the highly diastereoselective formation of a variety of all-cis-(multi)fluorinated piperidines and the study of their conformational behaviour.

    • Zackaria Nairoukh
    • , Marco Wollenburg
    • , Christoph Schlepphorst
    • , Klaus Bergander
    •  & Frank Glorius
    Nature Chemistry 11, 264-270
  • Research | | open

    Chiroptical sensing in complex mixtures remains a challenging task. Here, the authors report an efficient coumarin probe for chiroptical click chirality sensing of absolute configuration, concentration and enantiomeric excess of several compound classes. The method can be directly applied to crude asymmetric reaction mixtures.

    • F. Yushra Thanzeel
    • , Kaluvu Balaraman
    •  & Christian Wolf
  • Research |

    Widely used palladium-mediated cross-couplings typically operate via a handful of fundamental reaction steps. Now, the reactivity between palladium and C–C σ-bonds has been described. This carbopalladation enables the coupling of organoboronic esters and aryl triflates across a C–C σ-bond of a bicyclo[1.1.0]butane to form disastereomerically pure trisubstituted cyclobutanes.

    • Alexander Fawcett
    • , Tobias Biberger
    •  & Varinder K. Aggarwal
    Nature Chemistry 11, 117-122

News and Comment

  • News and Views |

    Strained boronate complexes have now been shown to enable an unprecedented cross-coupling reaction across a C–C σ-bond. Using this approach, highly functionalized cyclobutanes can be prepared with excellent stereocontrol from readily available reagents.

    • Alejandro Parra
    •  & Mariola Tortosa
    Nature Chemistry 11, 104-106
  • News and Views |

    Optimization of catalytic stereoselectivity for new substrates often requires a time consuming experimental process, and high-accuracy molecular modelling remains intractable for comprehensive virtual screening. Now, highly enantioselective rhodium hydrogenation catalysts have been identified using a rapid computational transition-state analysis protocol and then experimentally verified.

    • Daniel H. Ess
  • News and Views |

    The preparation of three-dimensional frameworks with multiple stereocentres from simple acyclic hydrocarbons represents a challenging transformation. Now, starting from simple and readily available reagents, formation of these complex targets can be achieved in just three catalytic transformations with high levels of stereocontrol.

    • Laura Castoldi
    •  & Vittorio Pace
    Nature Chemistry 10, 1081-1082
  • News and Views |

    Knots have been rigorously studied since the 1860s, but only in the past 30 years have they been made in the laboratory in molecular form. Now, the most complex small-molecule examples so far — a composite knot and an isomeric link, each with nine crossings — have been prepared.

    • Edward E. Fenlon
    Nature Chemistry 10, 1078-1079
  • Comments and Opinion |

    Louis Pasteur was a scientific giant of the nineteenth century, but, as Joseph Gal asks, was his most famous contribution to the understanding of chemistry — chirality — influenced more by his artistic talents?

    • Joseph Gal
    Nature Chemistry 9, 604-605
  • News and Views |

    Planar molecules may break mirror symmetry when aligned on a surface, but both right- and left-handed forms will be created. Starting with a single-handed precursor, chiral adsorbates of planar hydrocarbons with a single handedness are formed in on-surface reactions.

    • Karl-Heinz Ernst
    Nature Chemistry 9, 195-196