Abstract
The condensation of readily available O-substituted carbamates with 2,5-dimethoxytetrahydrofuran gives N-alkoxycarbonyl pyrroles in a single step and in good yield. By this method, several common amine protecting groups can be introduced on the pyrrole nitrogen. With the exception of N-Boc, N-alkoxycarbonyl groups have seen only minimal use for protection of the pyrrole nitrogen to date. Here, we show that N-alkoxycarbonyl protection can endow pyrrole with distinct reactivity in comparison with N-sulfonyl protection, for example, in a pyrrole acylation protocol employing carboxylic acids with a sulfonic acid anhydride activator.
Original language | English |
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Pages (from-to) | 13584–13589 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 88 |
Issue number | 19 |
Early online date | 6 Oct 2023 |
DOIs | |
Publication status | Published - 6 Oct 2023 |
Funding
The authors thank EPSRC for a DTP PhD studentship to J.L.H. (EP/T518013/1). The authors acknowledge the Material and Chemical Characterization Facility (MC2) at the University of Bath (https://doi.org/10.15125/mx6j-3r54).
Funders | Funder number |
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Engineering and Physical Sciences Research Council | EP/T518013/1 |
University of Bath |
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Dataset for the Synthesis of N-alkoxycarbonyl pyrroles from O-substituted carbamates – A synthetically enabling pyrrole protection strategy
Hann, J. (Creator), Lewis, S. (Creator), Lyall, C. (Creator) & Kociok-Kohn, G. (Creator), University of Bath, 18 Aug 2023
DOI: 10.15125/BATH-01255
Dataset