Scheme 1. Synthetic Route to Cyclohexyl Quinolines.
Reagents and conditions: a. Pd(PPh3)4, K2CO3, dioxane, water, 100 °C, 16 h (77%); b. Pd/C (Degussa), NH4HCO2; c. 4 M HCl, Acetone (75% over 2 steps); d. NaBH4 (5:1 trans:cis dr); e. MsCl, Pyr. (76% over 2 steps); f. (i) NaH, di-tBu-malonate, (ii) AcOH, 130 °C (76%); g. PivCl, TEA; lithium-(R)-2-oxo-4-phenyloxazolidin-3-ide (85%); h. NaHMDS, −40 °C; MeI (>20:1 dr) (68%); i. LiOH, H2O2 (82%); j. DPPA, TEA; LiOH, H2O (90%)