ChemInform Abstract: Asymmetric Desymmetrization of meso-Pyrrolidine Derivatives by Enantiotopic Selective C—H Hydroxylation Using (Salen)manganese(III) Complexes.

✍ Scribed by T. Punniyamurthy; Tsutomu Katsuki

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 37 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199949032

✦ Synopsis

1999 stereochemistry stereochemistry (general, optical resolution) O 0030 49 -032 Asymmetric Desymmetrization of meso-Pyrrolidine Derivatives by Enantiotopic Selective C-H Hydroxylation Using (Salen)manganese(III) Complexes. -An efficient synthetic method for the asymmetric desymmetrization of meso-pyrrolidine derivatives is presented, involving the Mn(salen) complex-catalyzed oxidation of the meso-pyrrolidines (I), (IV), (VI), and (VIII) with iodosylbenzene and subsequent oxidation of the stereoselectively formed exo-α-hydroxypyrrolidines [cf. (II)] to the corresponding optically active lactams (III), (V), (VII), and (IX), resp., under Jones oxidation conditions. It is shown that N-protecting groups influence the stereoselectivity of oxidation. -(PUNNIYAMURTHY, T.; KATSUKI,