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

التفاصيل البيبلوغرافية
العنوان: Enantioselective synthesis of β-aryl-γ-lactam derivatives via Heck–Matsuda desymmetrization of N-protected 2,5-dihydro-1H-pyrroles
المؤلفون: Arnaldo G. de Oliveira Jr., Martí F. Wang, Rafaela C. Carmona, Danilo M. Lustosa, Sergei A. Gorbatov, Carlos R. D. Correia
المصدر: Beilstein Journal of Organic Chemistry, Vol 20, Iss 1, Pp 940-949 (2024)
بيانات النشر: Beilstein-Institut, 2024.
سنة النشر: 2024
المجموعة: LCC:Science
LCC:Organic chemistry
مصطلحات موضوعية: desymmetrization, enantioselective heck–matsuda reaction, lactam synthesis, n,n-ligands, palladium, Science, Organic chemistry, QD241-441
الوصف: 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.
نوع الوثيقة: article
وصف الملف: electronic resource
اللغة: English
تدمد: 1860-5397
Relation: https://doaj.org/toc/1860-5397
DOI: 10.3762/bjoc.20.84
URL الوصول: https://doaj.org/article/1b3a46b5e82d49d7a78d4ac8b8f6de51
رقم الأكسشن: edsdoj.1b3a46b5e82d49d7a78d4ac8b8f6de51
قاعدة البيانات: Directory of Open Access Journals
الوصف
تدمد:18605397
DOI:10.3762/bjoc.20.84