(S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE

Reactions

Catalyst for the enantioselective addition of diethylzinc to α,β-unsaturated aldehydes

Chemical Properties

white to slightly yellow crystalline powder

Uses

(S)-(+)-2-[Hydroxy(diphenyl)methyl]-1-methylpyrrolidine is used for chiral ligand for the enantioselective addition of dialkylzincs, alkynylzinc, and cyanomethylzinc bromide to aldehydes; chiral ligand for the enantioselective Reformatsky reaction; chiral ligand for the enantioselective Diels-Alder reaction; chiral auxiliary for asymmetric polymerization.

Preparation

Reaction of Phenylmagnesium Bromide with (S)-N-[(benzyloxy)carbonyl]proline methyl ester and subsequent reduction with Lithium Aluminum Hydride affords the (S)-(+)-2-[Hydroxy(diphenyl)methyl]-1-methylpyrrolidine in 83% overall yield.