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. Author manuscript; available in PMC: 2020 Sep 24.
Published in final edited form as: J Org Chem. 2013 Aug 29;78(18):9085–9092. doi: 10.1021/jo401171q

Table 2.

Asymmetric Dihydroxylation of Olefin 24

graphic file with name nihms-1626034-t0008.jpg
Ligands screeneda Compound 25, C25 ratio, epi:natural (R:S)
None 2.2:1
(DHQD)2PHAL 1:1
(DHQ)2PHAL 9.5:1 (82%)
(DHQD)2PYR 1:3.8
(DHQ)2PYR 2:1
DHQD 1.8:1
DHQ 2.5:1
a

Conditions: K2OsO4 (2 mol %), ligand (10 mol %), t-BuOH/H2O (1:1), 0 °C, 40 h.