Exploring Molecular Chirality Transfer

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The chirality of a molecule, acquired by the presence of central chirality, axial chirality, or planar chirality, plays an important role in materials chemistry, in the directed motion, in molecular recognition, and especially in the development of drugs. One chiral form of a drug (enantiomer) may be an effective agent against disease, while the other chiral enantiomer may not only be inactive but also toxic. Moreover, many naturally occurring molecules such as amino acids, sugars, and biologically relevant molecules i.e. DNA, RNA, and proteins are also chiral. Therefore, it is highly desirable for synthetic organic chemists to have access to chiral materials. Taking inspiration from the control of chirality and using numerous processes that can be mediated by transition metals, in this work we have discussed various aspects of chirality transfer for the development of directed motions in a molecular machine and the asymmetric synthesis of several important molecules. For example, we have applied it to the development of chemically driven rotatory molecular motors based on a biaryl system (where the central chirality is transferred to the axial chirality of a biaryl). We have also developed methods for the asymmetric synthesis of several important compounds such as chiral phosphine and amine derivatives (where axial chirality is transferred to central chirality). In addition to asymmetric transformations, we have successfully used organolithium reagents in a Pd-catalyzed process for the synthesis of versatile benzylalkynes and substituted allenes.
Original languageEnglish
QualificationDoctor of Philosophy
Awarding Institution
  • University of Groningen
  • Feringa, Ben L., Supervisor
  • Harutyunyan, Syuzanna, Supervisor
Award date13-Dec-2021
Place of Publication[Groningen]
Publication statusPublished - 2021

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