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. 2015 Apr 13;54(21):6217–6221. doi: 10.1002/anie.201501394

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© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

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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.