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. Author manuscript; available in PMC: 2018 Sep 13.
Published in final edited form as: J Am Chem Soc. 2017 Aug 30;139(36):12422–12425. doi: 10.1021/jacs.7b07745

Scheme 2. Chemoselective Reactions of Heterocycloadducts*.

Scheme 2

*Conditions: aNaBH4 (0.33 equiv), THF, 0 °C; bBr2 (2.0 equiv), Me2S (2.5 equiv), CH2Cl2, 0 °C to rt; cOsO4 (1 mol %), NMO (6.0 equiv), THF/acetone/H2O (5:5:1), 0 °C to rt; di. Pd/C (10 wt %), AcOH (5.0 equiv), MeOH, rt, ii. HCl in 1,4-dioxane (4 N, 25.0 equiv), rt; emCPBA (1.5 equiv), NaHCO3 (2.0 equiv) CH2Cl2, rt; fHONH2· HCl (1.5 equiv), NaOAc (2.0 equiv), THF, rt; gNaBH4 (2.0 equiv), anhydrous MeOH, 0 °C; hp-O2NC6H4COCl (2.2 equiv), TEA (3 equiv), DMAP (10 mol %), anhydrous THF, rt; iNaH (60 wt %, 1.1 equiv), Me3SO·I (1.1 equiv), anhydrous THF, 0 °C.