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letter
. 2014 Jun 11;10:1333–1338. doi: 10.3762/bjoc.10.135

Figure 6.

Figure 6

Synthesis of 21 and 22, 3-arylcyclohexylamine derivatives of PreQ0. Reagents and conditions: (a) PhB(OH)2, Pd(OAc)2, bpy, H2O/THF/AcOH, 3 days, 60 °C, 98%; (b) K-Selectride, THF, 2 h, −90 °C; then KOH (aq), H2O2, 30 min, rt, 80%, 99% ds; (c) LiAlH4, Et2O, 1,5 h, 0 °C to rt; then NaOH (aq), 30 min, rt, 76%, 97% ds (d) MsCl, Et3N, THF, 16 h, rt, (trans- 67%, cis- 64%); (d) NaN3, DMF, 2 days, 80 °C, (trans- 56%, cis- 67%); (f) HCO2NH4, Pd/C, MeOH, 1.5 h, reflux, (trans- 92%, cis- 94%); (g) 9, Et3N, n-BuOH, 16 h, 130 °C; (h) KOH, n-BuOH/EtOH, 16 h, 80 °C, (trans- 38%, cis- 50%).