1: 1) sodium hydride / 1) DMSO, room temp., 30 min, 2) DMSO, 8 h 2: 1) sodium ethoxide / 1) ethanol, reflux, 2) reflux, 3 h 4: 71.4 percent / 2percent aq. NaOH / ethanol; H2O / 3 h / Heating View Scheme

β-Ι-9-BBN 1) pentane, -78 deg C, 1 h 2) -78 deg C, 30 min then r.t., 1 h; Yield given. Multistep reaction;

1: 1) sodium hydride / 1) DMSO, room temp., 30 min, 2) DMSO, 8 h 2: 1) sodium ethoxide / 1) ethanol, reflux, 2) reflux, 3 h View Scheme

chiral copper N-heterocyclic carbene in diethyl ether; hexane T=-78°C; 16 h;