A catalytic aldol reaction and condensation through in situ boron "Ate" complex enolate generation in water

General experimental details All starting materials were obtained commercially from Aldrich, Lancaster or Fluka and were used as received or prepared by known methods, unless otherwise stated. Solvents were also used as received or dried by known methods, unless otherwise stated. In the case of DCM and toluene this involved refluxing over CaCO3 under argon and in the case of ether and THF involved refluxing over sodium and benzophenone under argon, or using a commercial drying system. Purification by column chromatography was performed using Lancaster silica gel with pore size 60 Å, 40 Å or Florasil®. TLC was carried out using Merck aluminium-backed or plastic-backed pre-coated plates. TLC plates were analysed by UV at 254 and 365 nm, and visualisation was performed using standard solutions of 4- anisaldehyde, vanillin or PMA. NMR spectra were recorded at 200, 300 or 400 MHz using a Varian Mercury 200 MHz spectrometer, Varian Unity 300 MHz spectrometer or a Brucker 400 MHz spectrometer, respectively, unless otherwise stated. Chemical shifts are expressed as parts per million (ppm) downfield from the internal standard TMS for 1 H and 13 C, to external BF3.Et2O for 11 B. Electrospray (ES) mass spectra were recorded using a Micromass LCT spectrometer. Infra red spectra were obtained using FT1600 series spectrometer. Ultra-violet spectra were measured using a Unicam UV-Vis UV2 spectrometer. Melting points were measured with an Electrothermal apparatus and were uncorrected. Evaporations were carried out at 20 mmHg using a Büchi rotary evaporator and water bath, followed by evaporation to dryness under vacuum (<2 mmHg). N-Butyl-2-(2-boronophenyl)benzimidazole sodium hydroxide complex 2