Synthesis of 4‐(R)‐Naphthalene‐2‐yloxy‐1‐(1‐Phenyl‐(S)‐Ethyl)‐Pyrrolidin‐3‐(R)‐ol and 4‐(S)‐Naphthalen‐2‐yloxy‐1‐(1‐Phenyl‐(S)‐Ethyl)‐Pyrrolidin‐3‐(S)‐ol: Versatile Chiral Intermediates for Synthesis

A convenient and rapid synthesis of 4‐(R)‐(naphthalen‐2‐yloxy)‐1‐(1‐phenyl‐(S)‐ethyl)‐pyrrolidin‐3‐(R)‐ol and 4‐(S)‐(naphthalen‐2‐yloxy)‐1‐(1‐phenyl‐(S)‐ethyl)‐pyrrolidin‐3‐(S)‐ol is disclosed. The reaction scheme is highlighted by the meso‐epoxidation of 1‐(1‐phenyl‐(S)‐ethyl)‐2,5‐dihydro‐1H‐pyrrole followed by addition of 2‐naphthol alkoxide to provide both expected diastereoisomers. Separation of the diastereoisomers by crystallization provided access to both diastereoisomers in modest yield without the employment of expensive chiral catalysts. X‐ray analysis of one of the diastereoisomers led to the unambiguous assignment of each diastereoisomer. These chiral pyrrolidine analogues should be useful as intermediates in natural product, combinatorial/parallel synthesis, and medicinal chemistry.