General procedure for the synthesis of (S)-(-)-3-butyn-2-ol from 3-butyn-2-ol: a substrate solution containing racemic 3-butyn-2-ol (10 g, 0.143 mol) and vinyl benzoate (41.53 g, 0.28 mol) was prepared in a total volume of 50 ml. 2.5 g of Europa lipase E2 was added to the solution ( Candida rugosa lipase). The mixed solution was placed on a shaker at 23°C (ambient temperature) for stirring the reaction. The progress of the reaction was monitored by chiral GC on a Varian CP7503 Chiralsil Dex CB column (30m x 0.32um) using helium as carrier gas at a pressure of 9.52 psi and an initial flow rate of 2 ml/min. GC conditions: initial column temperature of 50°C was held for 5 min, then ramped up at a rate of 20°C/min to 180°C and held for 2 minutes. The total run time was 13.5 min. The retention times of the components were as follows: 5.6 min corresponded to (R)-3-butyn-2-ol, 5.9 min corresponded to (S)-3-butyn-2-ol, 11.51 min corresponded to (R)-benzyl ester and 11.56 min corresponded to (S)-benzyl ester. After incubation of the reaction for 48 hours, an ee value of 96% was obtained at 75% conversion for (S)-3-butyn-2-ol.
[1] Tetrahedron: Asymmetry, 1993, vol. 4, # 7, p. 1645 - 1650
[2] Tetrahedron Asymmetry, 1998, vol. 9, # 24, p. 4429 - 4439
[3] Patent: WO2005/108346, 2005, A1. Location in patent: Page/Page column 7
