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

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Abstract

I would like to start this elaborate by posing the most fundamental question: why do we study chirality? The answer is because Nature is chiral and, as part of it ourselves, it is imperative to understand it and its chiral mechanisms.

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Notes

  1. 1.

    For further reading on heteroatoms chirality see: Wolf [3].

  2. 2.

    For more noteworthy examples of controlled central chirality see: (a) Enders et al. [6]; (b) Cassani et al. [7]; (c) Zhou et al. [8]; (d) Chauhan et al. [9]; (e) Reyes et al. [10].

  3. 3.

    The priority of substituents is assigned according to the CIP rules. Angew. Chem. Int. Ed., 1966, 385.

  4. 4.

    (a) Betson et al. [20]; (b) Clayden et al. [21].

  5. 5.

    For exhaustive reviews on helically chiral compounds see: (a) Shen and Chen [25]; (b) Gingras [26], 968; (c) Gingras et al. [27]; (d) Gingras [26], 1051.

  6. 6.

    (a) MacMillan [38]; (b) List [39].

  7. 7.

    For exhaustive reading on asymmetric aminocatalysis on both enamine and iminium ion reactions see: Science of synthesis “Asymmetric organocatalysis 1—Lewis base and acid catalysis”, Thieme, 2012.

  8. 8.

    For a better understanding of the concept, instead of drawing two mechanisms for the endo and exo products, a single one is reported with a generic nucleophile “NuH”. Also, the enantiotopic faces of the iminium ion may change depending on the nature of the R substituent.

  9. 9.

    For reviews on NHC-catalysis see: (a) Biju et al. [42]; (b) Grossman and Enders [43]; (c) Chen and Ye [44]; (d) Hopkinson et al. [45]; (e) Wang and Scheidt [46].

  10. 10.

    For reviews on MBH and MBH-like reactions see: (a) Wei and Shi [47]; (b) Rios [48].

  11. 11.

    (a) For an exhaustive reading on Brønsted acid/base catalysis see: Rueping et al. [51]; (b) Science of synthesis “Asymmetric organocatalysis 2 – Brønsted base and acid catalysis, and additional topics”, Thieme, 2012.

  12. 12.

    For reviews on ACDC see: (a) Phipps et al. [56]; (b) Mahlau and List [57].

  13. 13.

    For exhaustive reviews on PTC see: (a) Ooi and Maruoka [59]; (b) Shirakawa and Maruoka [60]; (c) Albanese et al. [61].

  14. 14.

    Asymmetric PTC is believed to mainly follow the “interfacial mechanism” which is the only one reported for simplicity. See: Kitamura et al. [62]. For reading on the “extraction mechanism” see: Starks [63].

  15. 15.

    For reviews see: (a) Doyle and Jacobsen [65]; (b) Knowles and Jacobsen [66].

  16. 16.

    (a) Sigman and Jacobsen [67]; (b) Corey and Grogan [68].

  17. 17.

    For reviews see: (a) Shao and Zhang [69]; (b) Zhong and Shi [70]; (c) Allen and MacMillan [71]; (d) Du [72]; (e) Afewerki and Còrdova [73].

  18. 18.

    For some remarkable examples of dual catalysis see: (a) Krautwald et al. [74]; (b) Rono et al. [75]; (c) Noesborg et al. [76]; (d) Meazza et al. [77].

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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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Correspondence to Nicola Di Iorio .

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Di Iorio, N. (2018). Introduction. 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_1

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