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. 2024 Apr 5;89(8):5573–5588. doi: 10.1021/acs.joc.4c00067

Table 1. Screening Results for Different Dihydroxylation (DH) Conditions and Octenitol Substrates 12–14 on Analytical Scale.

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a

Isolated yield over 2 steps.

b

Product ratio determined upon deprotection via integration from 13C NMR (see Figure 5).

c

Upjohn conditions: K2[OsO2(OH)4] (1 mol %), NMO·H2O (1 equiv), t-BuOH/H2O (1:1, 0.1–0.3 M), rt.

d

Sharpless conditions A: AD-mix-α (×3) (1.4 g/mmol substrate), MsNH2 (2 equiv), t-BuOH/H2O/DCM (1:1:1, 0.3 M), rt.

e

Sharpless conditions B: AD-mix-β (×3) (1.4 g/mmol substrate), MsNH2 (2 equiv), t-BuOH/H2O/DCM (1:1:1, 0.3 M), rt.

f

t-BuOH/H2O/DCM (1:1:1) solvent mixture used; deprotection toward analysis: (a) NaOMe (30% in MeOH), MeOH, rt, 1 h; (b) H2 (1 atm), Pd/C (10 wt %), MeOH, rt, 18 h; and (c) Dowex-H+, H2O, 80 °C, 2 h.