Anodic a-methoxylations of (3Ä)-l-methoxycarbonylpyrrolidin-3-ol and two O-protected analogs display modest regioselectivities (yield of 3 s 54%; yield of 4< 72%). Substitution of the 2-methoxy group with a cyano group causes enhanced eis stereoselectivity (86%) when a terf-butyldimethylsilyloxy substituent was present in the 3-position. Hydrolysis of the isomeric cyano compounds gave cú-3-hydroxy-L-proline and íranj-3-hydroxy-D-proline.