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. 2016 May 16;7(8):5530–5536. doi: 10.1039/c6sc00932h

Scheme 1. Preparation of the quaternary ammonium compound 8a. Reagents and conditions: (a) Boc2O (3.0 equiv.), TEA (1.1 equiv.), DMAP (0.2 equiv.), DCM, RT, 14 h, 89%; (b) LDA (1.2 equiv.), propargyl bromide 12 (2.5 equiv.), –78 °C to RT, 2 h, THF; (c) TFA (5.0 equiv.), DCM, RT, 16 h; 58% over two steps; (d) LiAlH4 (3.0 equiv.), THF, 80 °C, 1 h, 85%; (e) PPh3AuNTf2 (5 mol%), 14 (2.0 equiv.), MsOH (1.3 equiv.), TFA (1.1 equiv.), AgOTf (2 mol%), DCE, RT, 6 h; then NaHCO3 (sat.), AgOTf (1.0 equiv.), RT, 73%.

Scheme 1