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Synlett 1999; 1999(11): 1775-1777
DOI: 10.1055/s-1999-2958
DOI: 10.1055/s-1999-2958
letter
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Catalytic Enantioselective Synthesis of the Phosphodiesterase Type IV Inhibitor (R)-(-)-Rolipram via Intramolecular C-H Insertion Process
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Publication History
Publication Date:
31 December 1999 (online)
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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.
(R)-(-)-rolipram - phosphodiesterase inhibitor - enantioselective synthesis - chiral dirhodium(II) catalyst - C-H insertion