1: 50 percent aq. NaOH; cetyltrimethylammonium chloride / 18 h / 80 °C 2: aq. conc. HCl / methanol / 2 h / 20 °C 3: K2CO3 / methanol / 0.17 h / 20 °C 4: 79 percent / tetrahydrofuran / 12 h / 20 °C 5: 79 percent / NaN3 / 15-crown-5 / tetrahydrofuran / 12 h / 20 °C 6: Jones' reagent / acetone / 0.25 h / 0 °C 7: H2 / Pd/C / ethanol / 16 h / 20 °C View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1.1: sodium iodide / acetonitrile / 0.08 h / 20 &deg;C / |Inert atmosphere<br />1.2: 20 &deg;C / |Inert atmosphere<br />2.1: C₅₂H₅₈; tri-tert-butyl phosphine; hydrogen / hexane / 24 h / 30003 Torr<br /> <br /> &nbsp;

<b>With</b>&nbsp; [((4S,4S)-Ph-BOX)ZnOMe](at)SBA-15₋₇₀₀&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1740230', constants.ctx, '0')">[D₃]acetonitrile</a> <br />T=60&deg;C;&nbsp;5&nbsp;h;&nbsp;&nbsp;Inert atmosphereGlovebox;&nbsp;&nbsp;Reagent/catalyst;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1738613', constants.ctx, '0')">tri-tert-butyl phosphine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '23557243', constants.ctx, '0')">C₅₂H₅₈</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '9960237', constants.ctx, '0')">Piers’ borane</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '969132', constants.ctx, '0')">pentane</a> <br />T=50&deg;C;&nbsp;P=30003&nbsp;Torr;&nbsp;24&nbsp;h;&nbsp;&nbsp;Autoclave;&nbsp;&nbsp;Catalytic behavior;&nbsp;&nbsp;Reagent/catalystSolvent;&nbsp;&nbsp;enantioselective reaction;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '14581698', constants.ctx, '0')">iron(III) trifluoromethanesulfonate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '4151241', constants.ctx, '0')">NaBEt₃H</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '7952025', constants.ctx, '0')">(4'S,5'S)-2,2-bis[4'-hydroxymethyl-5'-phenyl-1',3'-oxazolin-2'-yl]propane</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=-20 - 20&deg;C;&nbsp;16&nbsp;h;&nbsp;&nbsp;Inert atmosphereSchlenk technique;&nbsp;&nbsp;Overall yield = 90 percent; Optical yield = 2 percent ee; enantioselective reaction;&nbsp;<br /> &nbsp;