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Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ-Lactams.

ABSTRACT: Metal-catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current hydrogenation strategies are limited to the formation of C-H and N-H bonds. The stepwise addition of hydrogen yields reactive unsaturated intermediates that are rapidly reduced. In contrast, the interruption of complete hydrogenation by further functionalization of unsaturated intermediates offers great potential for increasing chemical complexity in a single reaction step. Overcoming the tenet of full reduction in arene hydrogenation has been seldom demonstrated. In this work we report the synthesis of sought-after, enantioenriched δ-lactams from oxazolidinone-substituted pyridines and water by an interrupted hydrogenation mechanism.

SUBMITTER: Wagener T

PROVIDER: S-EPMC7986189 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ-Lactams.

Wagener Tobias T Lückemeier Lukas L Daniliuc Constantin G CG Glorius Frank F

Angewandte Chemie (International ed. in English) 20210212 12

Metal-catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current hydrogenation strategies are limited to the formation of C-H and N-H bonds. The stepwise addition of hydrogen yields reactive unsaturated intermediates that are rapidly reduced. In contrast, the interruption of complete hydrogenation by further functionalization of unsaturated intermediates offers great potential for increasing chemical complexity in a single reactio ...[more]

PMID: 33460521

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