Acta Chemica Scandinavia

Anodic Methoxylation of Pyrrolidinol Derivatives/Enantioselective Synthesis of eis-and f/an¿{3fl)-3-Hydroxyprolines

M Thaning, LG Wistrand

Index: Thaning, Mikkel; Wistrand, Lars-G. Acta Chemica Scandinavica, 1989 , vol. 43, # 3 p. 290 - 295

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Citation Number: 54

Abstract

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.