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Chiral Phosphoramidites Enable Pd-catalyzed Asymmetric Allylic C-H Functionalization Reactions

Allylic C-H activation; palladium catalysis；asymmetric catalysis；phosphoramidite

Phosphorus in Synthetic Chemistry > 2) Phosphorus compounds as ligands

Asymmetric allylic substitution has been one of the most robust coupling reactions to build up molecular complexity from readily available substances[1]. Basically, activated precursors of π-allyl fragments, including allylic halides, esters, carbonates, and even allylic alcohols, are competent substrates. Although great advances have been made in the allylic C-H functionalization over the last decades, the stereochemical control still represents a longstanding challenge. At this symposium, Pd-catalyzed asymmetric allylic C-H functionalization reactions enabled by chiral phosphoramidites will be described [2-4].

References

1. (a) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.


2. Wang, P.-S.; Gong, L.-Z. Acc. Chem. Res. 2020, 53, 2841. (b) Wang, T.-C.; Zhu, L.; Luo, S.-W.; Nong, Z.-S.; Wang, P.-S.; Gong, L.-Z. J. Am. Chem. Soc. 2021, 143, 20454. (c) Nong, Z.-S.; Zhu, L.; Wang, T.-C.; Fan, L.-F.; Wang, P.-S.; Gong, L.-Z. Nat. Synth. 2022, 1, 487.


3. (a) Tao, Z.-L.; Li, X.-H.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2015, 137, 4054; (b) Li, L.-L.; Tao, Z.-L.; Han, Z.-Y.; Gong, L.-Z. Org. Lett. 2017, 19, 102; (c) Wang, T.-C.; Wang, P.-S.; Chen, D.-F.; Gong, L.-Z. Sci China Chem, 2022, 65, 298; (d) Liu, R.: Shen, M.-L.: Fan, L.-F.; Zhou, X.-L.; Wang, P.-S.; Gong, L.-Z. Angew. Chem., Int. Ed. 2023, 62, e202211631.


4. Fan, L.-F.; Xie, P.-P.; Wang, P.-S.; Hong, X.; Gong, L.-Z. CCS Chem. 2021, 3, 1166.