4-Fluoroprolines are among the most useful nonnatural amino acids in chemical biology. Here, practical routes are reported for the synthesis of the 2S,4R, 2S,4S, and 2R,4S diastereomers of 4-fluoroproline. Each route starts with (2S,4R)-4-hydroxyproline, which is a prevalent component of collagen and hence readily available, and uses a fluoride salt to install the fluoro group. Hence, the routes provide process-scale access to these useful nonnatural amino acids.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2598397 | PMC |
| http://dx.doi.org/10.1016/j.jfluchem.2008.06.024 | DOI Listing |
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