Details

Autor(en) / Beteiligte

• de Oliveira, Arnaldo G
• Wang, Martí F
• Carmona, Rafaela C
• Lustosa, Danilo M
• Gorbatov, Sergei A
• Correia, Carlos R D

Titel

Enantioselective synthesis of β-aryl-γ-lactam derivatives via Heck-Matsuda desymmetrization of N-protected 2,5-dihydro-1H-pyrroles

Ist Teil von

• Beilstein journal of organic chemistry, 2024-04, Vol.20 (1), p.940-949

Ort / Verlag

Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany: Beilstein-Institut

Erscheinungsjahr

2024

Quelle

EZB-FREE-00999 freely available EZB journals

Beschreibungen/Notizen

• We report herein an enantioselective palladium-catalyzed Heck-Matsuda reaction for the desymmetrization of N-protected 2,5-dihydro-1H-pyrroles with aryldiazonium salts, using the chiral N,N-ligand (S)-PyraBox. This strategy has allowed straightforward access to a diversity of 4-aryl-γ-lactams via Heck arylation followed by a sequential Jones oxidation. The overall method displays a broad scope and good enantioselectivity, favoring the (R) enantiomer. The applicability of the protocol is highlighted by the efficient enantioselective syntheses of the selective phosphodiesterase-4-inhibitor rolipram and the commercial drug baclofen as hydrochloride.