Catalytic Enantioselective Synthesis of the Phosphodiesterase Type IV Inhibitor (R)-(-)-Rolipram via Intramolecular C-H Insertion Process

1 November 1999

journal article
letter
Published by Georg Thieme Verlag KG in Synlett

Vol. 1999 (11) , 1775-1777
https://doi.org/10.1055/s-1999-2958

Abstract

A new route to the phosphodiesterase type IV inhibitor (R)-(-)-rolipram (1) has been developed, wherein the key step relies on enantioselective intramolecular C-H insertion of N-alkyl-N-4-nitrophenyl-α-methoxycarbonyl-α-diazoacetamide 7 catalyzed by chiral dirhodium(II) complex. The dirhodium(II) carboxylate, Rh₂(S-BPTTL)₄, incorporating N-benzene-fused-phthaloyl-(S)-tert-leucinate as a bridging ligand has proven to be the catalyst of choice for this process, providing the desired 2-pyrrolidinone 8 in 88% ee.

Keywords

(R)-(-)-ROLIPRAM
PHOSPHODIESTERASE INHIBITOR
ENANTIOSELECTIVE SYNTHESIS
CHIRAL DIRHODIUM(II) CATALYST
C-H INSERTION

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