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. 2023 Oct 24;145(44):24021–24034. doi: 10.1021/jacs.3c07163

Scheme 6. Oxygenation of trans-6-tert-Butylspiro[2.5]octan-2-ol (P8a-OH) and cis-6-tert-Butylspiro[2.5]octan-2-ol (P8c-OH).

Scheme 6

Conversion and product yields were determined by GC and averaged over two independent experiments. (a) Reaction conditions: P8a-OH or P8c-OH 1 equiv, oxone 1 equiv, NaHCO3 4 equiv, 1,1,1-trifluoro-2-butanone 0.2 equiv, HFIP/H2O (3:1), Bu4NHSO4 0.05 equiv, T = 0 °C, 3 h. (b) P8a-OH 1 equiv, P8c-OH 1 equiv, oxone 1 equiv, NaHCO3 4 equiv, 1,1,1-trifluoro-2-butanone 0.2 equiv, HFIP/H2O (3.0:1.0), Bu4NHSO4 0.05 equiv, T = 0 °C, 6 h. rsm: recovered starting material.