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Direct Catalytic Synthesis of C(Sp2)–C(Sp3) Atropisomers with Simultaneous Control of Central and Axial Chirality

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New Organocatalytic Strategies for the Selective Synthesis of Centrally and Axially Chiral Molecules

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Abstract

In the previous chapter, we discussed about the synthesis of axially chiral compounds using an indirect method to generate a stereogenic axis. The key point was to break the symmetry of a molecule and “reveal” the blocked rotation of a single sp2–sp2 bond.

Di Iorio et al. [1].

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Notes

  1. 1.

    For other examples of indirect generation of stereogenic axes see: Refs. [2,3,4,5].

  2. 2.

    For a stable atropisomer (at 25 °C) the rotational barrier should be higher than 25 kcal/mol

  3. 3.

    Compound 221 shows fast degradation in DMSO and determination of the rotational barrier was impossible so the value is calculated for the corresponding OAc structure

  4. 4.

    Also the experimental barriers reported in references [12,13,14,15,16,17] are very high (>30 kcal/mol) for compounds similar to ours.

  5. 5.

    In Ref. [18], catalyst 140 had already been identified as the best amine so we did not perform an amine screening

  6. 6.

    See the experimental section for details.

References

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Authors and Affiliations

  1. Department of Industrial Chemistry “Toso Montanari”, University of Bologna, Bologna, Italy

    Nicola Di Iorio

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  1. Nicola Di Iorio
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Correspondence to Nicola Di Iorio .

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Di Iorio, N. (2018). Direct Catalytic Synthesis of C(Sp2)–C(Sp3) Atropisomers with Simultaneous Control of Central and Axial Chirality. In: New Organocatalytic Strategies for the Selective Synthesis of Centrally and Axially Chiral Molecules. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-74914-3_4

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