Catalyst selective and regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates: synthetic and computational studies Public Deposited

http://ir.library.oregonstate.edu/concern/articles/8336h3897

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  • The regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates is described, with DMAP giving preferential N-carboxylation and triazolinylidenes promoting selective C-carboxylation (both with up to >99 : 1 regioselectivity). An enantioselective O- to C-carboxyl variant using NHC catalysis is demonstrated (up to 92% ee), while mechanistic and DFT studies outline the pathways operative in this system and provide insight into the reasons for the observed selectivity.
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  • Gould, E., Walden, D. M., Kasten, K., Johnston, R. C., Wu, J., Slawin, A. M., ... & Smith, A. D. (2014). Catalyst selective and regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates: synthetic and computational studies. Chemical Science, 5(9), 3651-3658. doi:10.1039/C4SC00879K
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