A strategy to synthesize allenylphosphine derivatives with both P and axial chirality is developed and allows for diverse derivatizations of chiral phosphines. The Ni-catalysed enantioconvergent reaction occurs without racemization or symmetrization of the propargylic carbonate substrate, as demonstrated by combined experimental and computational methods.
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References
Swamy, K. C. K., Anitha, M., Debnath, S. & Shankar, M. Reactivity of allenylphosphonates/allenylphosphine oxides — some new addition/cycloaddition and cyclization pathways. Pure Appl. Chem. 91, 773–784 (2019). This paper highlights addition and cycloaddition reactions of allenylphosphonates or allenylphosphine oxides.
Chan, V. S., Chiu, M., Bergman, R. G. & Toste, F. D. Development of ruthenium catalysts for the enantioselective synthesis of P-stereogenic phosphines via nucleophilic phosphido intermediates. J. Am. Chem. Soc. 131, 6021–6032 (2009). This paper illustrates the poisoning effects, namely catalyst inhibition and background reactions, caused by trivalent phosphines.
Ito, H., Kunii, S. & Sawamura, M. Direct enantio-convergent transformation of racemic substrates without racemization or symmetrization. Nat. Chem. 2, 972–976 (2010). This paper reports a Cu-catalysed enantioconvergent allylic borylation without racemization or symmetrization of allylic ethers.
Liu, X.-T., Zhang, Y.-Q., Han, X.-Y., Sun, S.-P. & Zhang, Q.-W. Ni-catalyzed asymmetric allylation of secondary phosphine oxides. J. Am. Chem. Soc. 141, 16584–16589 (2019). This paper reports a Ni(0)-catalysed asymmetric allylic substitution of secondary phosphine oxides.
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This is a summary of: Wang, W.-H. et al. Enantioselective synthesis of P-stereogenic allenylphosphines through Ni-catalysed propargylic substitution. Nat. Synth. https://doi.org/10.1038/s44160-022-00123-3 (2022).
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Enantioconvergent synthesis of P-stereogenic allenylphosphines. Nat. Synth 1, 680–681 (2022). https://doi.org/10.1038/s44160-022-00127-z
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DOI: https://doi.org/10.1038/s44160-022-00127-z
