(1R)-1-phenylbut-3-en-1-ol

Conditions: temp:-74.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.25 mmol of the titanium compound of Example 1b in 120 ml of diethyl ether is cooled to -74° C. and 0.2 ml (2.0 mmol) of freshly distilled benzaldehyde is added. The beige suspension is stirred for a further 2 hours at -74° C. and 5 ml of a 5N H2O/THF solution are added. The beige suspension is warmed to RT, stirred for a further hour at this temperature, filtered with suction and concentrated on a rotary evaporator. The crude product (1.53 g of yellow-brown oil) is flash-chromatographed twice (80 g of silica gel, 25 cm long, cross-section 2 cm, 10 ml/fraction, 0.5 bar, 20:1 toluene/ethanol); (50 g of silica gel, 25 cm long, cross-section 2 cm, 15 ml/fraction, 0.5 bar, 15:1 toluene/ethanol). 0.2 g of product are obtained. Yield: 66%, ee: 82%. The beige suspension is warmed to RT stirred for a further hour at this temperature filtered with suction concentrated on a rotary evaporator The crude product (1.53 g of yellow-brown oil) is flash-chromatographed twice (80 g of silica gel, 25 cm long

Conditions: temp:-74.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.25 mmol of the titanium compound of Example 1b in 120 ml of diethyl ether is cooled to -74° C. and 0.2 ml (2.0 mmol) of freshly distilled benzaldehyde is added. The beige suspension is stirred for a further 2 hours at -74° C. and 5 ml of a 5N H2O/THF solution are added. The beige suspension is warmed to RT, stirred for a further hour at this temperature, filtered with suction and concentrated on a rotary evaporator. The crude product (1.53 g of yellow-brown oil) is flash-chromatographed twice (80 g of silica gel, 25 cm long, cross-section 2 cm, 10 ml/fraction, 0.5 bar, 20:1 toluene/ethanol); (50 g of silica gel, 25 cm long, cross-section 2 cm, 15 ml/fraction, 0.5 bar, 15:1 toluene/ethanol). 0.2 g of product are obtained. Yield: 66%, ee: 82%. The beige suspension is warmed to RT stirred for a further hour at this temperature filtered with suction concentrated on a rotary evaporator The crude product (1.53 g of yellow-brown oil) is flash-chromatographed twice (80 g of silica gel, 25 cm long

Conditions: temp:-74.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution in 100 ml of diethyl ether of 9.8 mmol of cyclopentadienylallyltitanium bis-(1,2:5,6-di-O-isopropylidene-α-glucofuranose) complex according to Example 1 is cooled to -74° C. by means of a CO2 /acetone bath, and 0.89 ml (8.8 mmol) of freshly distilled benzaldehyde is added. The clear yellow solution is stirred for a further 2 hours at -74° C., and 50 ml of NH4F solution (45% in water) are added. The beige emulsion is warmed to RT and separated in a separating funnel. The ether phase is extracted once with 50 ml and then with twice 30 ml of 2N HCl and is diluted with 300 ml of ether and is then washed with twice 300 ml of water and once with 300 ml of saturated NaCl solution, dried by means of MgSO4, filtered and evaporated to dryness on a rotary evaporator. The crude product is flash chromatographed (45 g of silica gel, 25 cm length, diameter 2 cm, 10 ml/fraction, 0.3 bar, 1:5 ether/n-hexane) and distilled (boiling point 150° C./14 mbar); 1.02 g (79% yield) of a clear, colourless oil are obtained: [α]D =+44.1° (c 6.5, benzene), 91% ee (methods A and B). The beige emulsion is warmed to RT separated in a separating funnel The ether phase is extracted once with 50 ml with twice 30 ml of 2N HCl and is diluted with 300 ml of ether is then washed with twice 300 ml of water and once with 300 ml of saturated NaCl solution dried by means of MgSO4 filtered evaporated to dryness on a rotary evaporator chromatographed (45 g of silica gel, 25 cm length, diameter 2 cm, 10 ml/fraction, 0.3 bar, 1:5 ether/n-hexane) and distilled (boiling point 150° C./14 mbar) 1.02 g (79% yield) of a clear, colourless oil are obtained

Conditions: temp:-74.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution in 100 ml of diethyl ether of 9.8 mmol of cyclopentadienylallyltitanium bis-(1,2:5,6-di-O-isopropylidene-α-glucofuranose) complex according to Example 1 is cooled to -74° C. by means of a CO2 /acetone bath, and 0.89 ml (8.8 mmol) of freshly distilled benzaldehyde is added. The clear yellow solution is stirred for a further 2 hours at -74° C., and 50 ml of NH4F solution (45% in water) are added. The beige emulsion is warmed to RT and separated in a separating funnel. The ether phase is extracted once with 50 ml and then with twice 30 ml of 2N HCl and is diluted with 300 ml of ether and is then washed with twice 300 ml of water and once with 300 ml of saturated NaCl solution, dried by means of MgSO4, filtered and evaporated to dryness on a rotary evaporator. The crude product is flash chromatographed (45 g of silica gel, 25 cm length, diameter 2 cm, 10 ml/fraction, 0.3 bar, 1:5 ether/n-hexane) and distilled (boiling point 150° C./14 mbar); 1.02 g (79% yield) of a clear, colourless oil are obtained: [α]D =+44.1° (c 6.5, benzene), 91% ee (methods A and B). The beige emulsion is warmed to RT separated in a separating funnel The ether phase is extracted once with 50 ml with twice 30 ml of 2N HCl and is diluted with 300 ml of ether is then washed with twice 300 ml of water and once with 300 ml of saturated NaCl solution dried by means of MgSO4 filtered evaporated to dryness on a rotary evaporator chromatographed (45 g of silica gel, 25 cm length, diameter 2 cm, 10 ml/fraction, 0.3 bar, 1:5 ether/n-hexane) and distilled (boiling point 150° C./14 mbar) 1.02 g (79% yield) of a clear, colourless oil are obtained

Conditions: temp:-74.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.25 mmol of the titanium compound of Example 1b in 120 ml of diethyl ether is cooled to -74° C. and 0.2 ml (2.0 mmol) of freshly distilled benzaldehyde is added. The beige suspension is stirred for a further 2 hours at -74° C. and 5 ml of a 5N H2O/THF solution are added. The beige suspension is warmed to RT, stirred for a further hour at this temperature, filtered with suction and concentrated on a rotary evaporator. The crude product (1.53 g of yellow-brown oil) is flash-chromatographed twice (80 g of silica gel, 25 cm long, cross-section 2 cm, 10 ml/fraction, 0.5 bar, 20:1 toluene/ethanol); (50 g of silica gel, 25 cm long, cross-section 2 cm, 15 ml/fraction, 0.5 bar, 15:1 toluene/ethanol). 0.2 g of product are obtained. Yield: 66%, ee: 82%. The beige suspension is warmed to RT stirred for a further hour at this temperature filtered with suction concentrated on a rotary evaporator The crude product (1.53 g of yellow-brown oil) is flash-chromatographed twice (80 g of silica gel, 25 cm long