Multi-step reaction with 10 steps
1.1: quinoline; hydrogen / ethyl acetate / 2 h
2.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere
3.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere
3.2: 3 h / -78 °C / Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere
5.1: lithium borohydride / methanol; dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere
6.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere
7.1: pyridine; indium; (1S,2R)-2-Amino-1,2-diphenylethanol / tetrahydrofuran; toluene / 0.75 h / -20 °C / Inert atmosphere
7.2: 16 h / Inert atmosphere
8.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere
9.1: dichloromethane / 2 h / 110 °C / Inert atmosphere
9.2: 0.33 h / Inert atmosphere
10.1: Mo(N)(OSi(C6H5)3)3(C5H5N) / toluene / 8 h / 110 °C / Inert atmosphere
With
pyridine; quinoline; indium; lithium borohydride; n-butyllithium; (1S,2R)-2-Amino-1,2-diphenylethanol; oxalyl dichloride; Mo(N)(OSi(C6H5)3)3(C5H5N); di-n-butylboryl trifluoromethanesulfonate; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; toluene;
2.1: Swern oxidation / 3.1: Evans aldol reaction / 3.2: Evans aldol reaction / 6.1: Swern oxidation / 7.1: Barbier reaction / 7.2: Barbier reaction;
DOI:10.1021/jo300225z