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a Performed with 1 (0,05 mmol) 2 (0,5mmol), 3 (1,5 mmol), 4 (0,05mmol) in 0,25 mL of solvent. b Determined by chiral stationary phase HPLC. When the reaction was performed in THF as solvent, the β-hydroxy carbonyl compound could be obtained with 90% ee and 56% yield (Entry 3). Decreasing the reaction temperature to -10 o C and -20 o C (entries 5 and 6) furnished desired product in 96% and 91% ee respectively. The Mukayama aldol reaction with silyl enol ether were carried out using 50 mol % of TBAF, figure 2.

Sequential organocatalytic -hydroxy and Mukayama addition: A perspective for the synthesis of Orlistat