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Studies on the Enantioselective Kinugasa Reaction: Efficient Synthesis of β-Lactams Catalyzed by N-PINAP/CuX Complexes.
- Source :
- European Journal of Organic Chemistry; Apr2016, Vol. 2016 Issue 12, p2212-2219, 8p
- Publication Year :
- 2016
-
Abstract
- 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 β-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. [ABSTRACT FROM AUTHOR]
- Subjects :
- LACTAMS
CHEMICAL synthesis
ENANTIOSELECTIVE catalysis
ALKYNES
NITRONES
CATALYSIS
Subjects
Details
- Language :
- English
- ISSN :
- 1434193X
- Volume :
- 2016
- Issue :
- 12
- Database :
- Complementary Index
- Journal :
- European Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 114816336
- Full Text :
- https://doi.org/10.1002/ejoc.201600050