Potassium Hydroxide → (S)-5-Phenyl-1-(triisopropylsilyl)pent-1-yn-3-ol

Participants

Reaction Steps

Following a modified procedure of Trost (Trost, B. M. et al., J. Am. Chem. Soc. 128, 6745-6754 (2006)); Potassium hydroxide (8.5 mg, 0.15 mmol, 1.2 mol %) and RuCl(p-cymene)[(S,S)-Ts-DPEN] (80.7 mg, 0.127 mmol, 1 mol %) were added to) PrOH (110 ml) and the resultant mixture was stirred for 2 min at r.t. 5-Phenyl-1-(triisopropylsilyl)pent-1-yn-3-one 84 (4.0 g, 12.7 mmol, 1 eq.) was added via syringe and the mixture was stirred at r.t. for 45 min. The mixture was concentrated in vacuo to give the crude product. This was purified by column chromatography on silica, eluting with petrol/Et2O (20:1 to 10:1), giving the title product 85 as a clear, colourless oil (4.0 g, 99%). The enantiomeric excess was determined to be 99% via HPLC analysis of its derivative 87. Analytical data consistent with the literature (Trost, B. M. et al., J. Am. Chem. Soc. 128, 6745-6754 (2006)).

Provenance & Evidence