A redox-neutral α-C-H oxygenation of commercially available pyrrolidin-3-ol with a monoprotected p-quinone generated an N-aryliminium ion intermediate, which reacted in situ with boronic acid nucleophiles to produce a series of cis-2-substituted pyrrolidin-3-ols. With this strategy, 8-epi-(-)-lentiginosine was synthesized from (3R,4R)-pyrrolidine-3,4-diol in three steps.
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| http://dx.doi.org/10.1021/acs.orglett.7b03807 | DOI Listing |
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