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Filtering by: DOI 10.1039/c5sc03796d License Attribution 3.0 United States

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

Creator:

Gould, Eoin, Walden, Daniel M., Kasten, Kevin, Johnston, Ryne C., Wu, Jiufeng, Slawin, Alexandra M., Mustard, Thomas J. L., Johnston, Brittany, Davies, Tony, Cheong, Paul Ha-Yeon, and Smith, Andrew D.

Abstract:

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...

Resource Type:

Article

Full Text:

carbonates: synthetic and computational studies. Chemical Science, 5(9), 3651-3658. doi:10.1039/C4SC00879K