Multi-step reaction with 9 steps
1.1: sodium acetate / 72 h / 20 °C / Inert atmosphere; Schlenk technique
2.1: tetrafluoroboric acid; (R,R)-(-)-1,2-bis[(o-methoxyphenyl)(phenyl) phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen / methanol / 18 h / 50 °C / 3750.38 Torr / Autoclave; Schlenk technique
3.1: thionyl chloride / methanol / 18 h / 0 - 80 °C / Inert atmosphere; Schlenk technique
4.1: sodium cyanoborohydride; acetic acid / methanol / 24 h / 20 °C / Molecular sieve; Inert atmosphere; Schlenk technique
5.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique
6.1: Dess-Martin periodane / dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique
7.1: chromium dichloride / tetrahydrofuran / 0.42 h / 200 °C / Inert atmosphere; Schlenk technique
7.2: 3 h / 20 °C
8.1: AD-mix-α; methanesulfonamide / water; tert-butyl alcohol / 72 h / 20 °C / Inert atmosphere; Schlenk technique
9.1: sodium periodate / dichloromethane; water / 2 h / 20 °C / Inert atmosphere; Schlenk technique
With
chromium dichloride; sodium periodate; lithium aluminium tetrahydride; tetrafluoroboric acid; thionyl chloride; (R,R)-(-)-1,2-bis[(o-methoxyphenyl)(phenyl) phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; methanesulfonamide; AD-mix-α; hydrogen; sodium acetate; sodium cyanoborohydride; Dess-Martin periodane; acetic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ml300385q