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Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ‐Lactams
Author(s) -
Wagener Tobias,
Lückemeier Lukas,
Daniliuc Constantin G.,
Glorius Frank
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202016771
Subject(s) - asymmetric hydrogenation , chemistry , catalytic hydrogenation , pyridine , catalysis , combinatorial chemistry , reactive intermediate , noyori asymmetric hydrogenation , hydrogen bond , organic chemistry , molecule , enantioselective synthesis
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.