Record Details
Catalyst selective and regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates: synthetic and computational studies
ScholarsArchive at Oregon State University
| Field | Value |
|---|---|
| Title | Catalyst selective and regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates: synthetic and computational studies |
| Names |
Gould, Eoin
(creator) Walden, Daniel M. (creator) Kasten, Kevin (creator) Johnston, Ryne C. (creator) Mustard, Thomas J. L. (creator) Johnston, Brittany (creator) Cheong, Paul Ha-Yeon (creator) et al. (creator) |
| Date Issued | 2014-09-01 (iso8601) |
| Note | This is the publisher’s final pdf. The journal is copyrighted by the Royal Society of Chemistry and the published article is licensed under a Creative Commons Attribute 3.0 Unported License. The published article can be found at: http://pubs.rsc.org/en/journals/journalissues/sc. |
| 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 the pathways operative in this system and provide insight into the reasons for the observed selectivity. |
| Genre | Article |
| Identifier | 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 |
