Abstract
In this article, a practically interesting route for the diastereoselective synthesis of phenylpropanolamines has been demonstrated for the first time. Using racemic O-tert-butyldiphenylsilyl (TBDPS) cyanohydrins as the starting materials, various syn phenylpropanolamines and derivatives (e.g., norpseudophedrine) have been successfully prepared in exellent diastereoselectivity via a practically interesting process.
GRAPHICAL ABSTRACT
Notes
a Reaction conditions: O-silyl cyanohydrin 1 (1 mmol), MeMgX (1.5 mmol) in a solvent (3 mL) at 0 °C for 10 h, and then MeOH (3 mL) and NaBH4 (2 mmol) for more 12 h at rt.
b Determined by GC using dodecane as internal stardard.
c Determined by GC or 1H NMR.
d nd, not detected.
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