(2S,2'S)-(-)-2-Hydroxymethyl-1-[(1-methylpyrrolidin-2-yl)-methyl]-pyrrolidine

(2S,2′S)-2-Hydroxymethyl-1-[(1-methylpyrrolidin-2-yl)methyl]pyrrolidine is a chiral ligand for alkyllithium, dialkylmagnesium, alkynyllithium, and functionalized organolithiums in the enantioselective addition to aldehydes; accelerates the basicity of alkyllithiums; catalyzes the addition of dialkylzinc to aldehyde.

Preparative Method of (2S,2′S)-2-Hydroxymethyl-1-[(1-methylpyrrolidin-2-yl)methyl]pyrrolidine: reduction of N-[N(-benzyloxycarbonyl)prolyl]proline methyl ester with Lithium Aluminum Hydride affords the title reagent in 81% yield.