AbstractEnantioselective syntheses of (R)‐antofine and (R)‐cryptopleurine starting from a 3‐phenanthrenylpropanal derivative are reported. Asymmetric α‐amination of this aldehyde is carried out in the presence of D‐proline, which constitutes the key step in the syntheses and resulted in the formation of the new stereogenic center with very high enantioselectivity (94% ee). The indolizidine and quinolizidine moieties in the target molecules are formed through Pictet‐Spengler reaction. The current method is shorter and high yielding in comparison with a similar strategy used for the synthesis of these molecules using proline‐catalyzed α‐hydroxylation of the same aldehyde.