(S)--Methyl-3-(1-methylethyl)benzenepropanal synthesis

Yield:-

Steps:

Multi-step reaction with 4 steps
1: potassium hydroxide / methanol / 13 h / 10 - 40 °C / Inert atmosphere
2: acetyl chloride / 8 h / 0 - 20 °C / Reflux; Inert atmosphere
3: copper(I) thiophene-2-carboxylate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / tetrahydrofuran / -78 °C / Inert atmosphere
4: sodium tetrahydroborate; water / Inert atmosphere

References:

Gremaud, Ludovic;Alexakis, Alexandre [Angewandte Chemie - International Edition,2012,vol. 51,# 3,p. 794 - 797]