Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 12, Pages 2212-2219Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600050
Keywords
Asymmetric synthesis; Lactams; Nitrones; Alkynes
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Funding
- National Science Centre Poland [DEC-2013/08/S/ST5/00569]
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Catalytic enantioselective Kinugasa reactions between acyclic and, for the first time, cyclic nitrones and terminal alkynes are described herein. A catalytic amount of the readily available PINAP/CuX complexes, generated in situ, efficiently catalyzed the Kinugasa reactions, leading to a series of beta-lactams with good enantioselectivities and moderate diastereoselectivities and yields. A broad range of nitrones and terminal alkynes, including the seldom reported alkyl-substituted alkynes, were tolerated under the reaction conditions. Further investigations proved that the PINAP/CuX catalytic system enabled the synthesis of monobactams on the gram scale (without loss of stereoselectivity and yield) and also both enantiomers by the appropriate choice of readily available atropisomeric N-PINAP ligands.
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