Scheme 3.

Organocatalytic enantioselective synthesis of BRD9 inhibitors. Reagents and conditions: a) 11, K₂CO₃, 68 (10 mol %), TBME, −20 °C, 70 %, d.r. 7:1, ee _major 90 %/ee _minor 90 %; b) TFA, CH₂Cl₂; c) DBU, CH₂Cl₂, 73 % (2 steps); d) NiCl₂⋅6 H₂O, NaBH₄, MeOH, 0 °C; e) Boc₂O, 74 % (2 steps); f) 4, K₃PO₄, CuI, (±)‐trans‐1,2‐diaminocyclohexane, 1,4‐dioxane, 97 °C, 65 %; g) HCl/dioxane, 96 %; h) RCl, TEA, CH₂Cl₂ or RNCO, CH₂Cl₂, 25–40 %. DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene, TBE=tert‐butyl methyl ether, TEA=triethylamine.