Multi-step reaction with 6 steps
1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 1.25 h / -30 °C / Inert atmosphere
1.2: 2 h / -78 - -40 °C
2.1: dmap / N,N-dimethyl-formamide / 16 h / 20 °C
3.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 16 h / 20 °C
4.1: triethylamine / dmap / dichloromethane / 18 h / 20 °C / Reflux
5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 14 h / 60 °C
6.1: triphenylphosphine; dicyclohexylmethylamine / N,N-dimethyl-formamide / 0.25 h
6.2: 5 h / 95 °C
With
n-butyllithium; dimethylsulfide borane complex; dicyclohexylmethylamine; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole;
dmap;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil;
3.1: Aldol Condensation;