期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 34, 页码 10644-10648出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b05045
关键词
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资金
- NSF [CHE-1665141, CHE-1152010]
- Vicki & Patrick F. Stone family
- National Science Foundation (NSF) [CHE-1352663, CHE-1102637]
The first highly selective catalytic hydroboration of alkyl-substituted aldimines to provide medicinally relevant alpha-amidoboronates is disclosed. The Cu(I)-catalyzed borylation proceeds with excellent facial selectivity when a set of planar-chiral N-heterocyclic carbenes (NHCs) were employed as ligands. Density functional theory computations suggest that interactions between BPin and the planar-chiral catalyst are responsible for the observed stereoselectivity. Important pharmacophores, such as the boronate analogue of isoleucine, can be prepared using a chromatography-free protocol starting from commercially available reagents. The application of these NHC ligands in these Cu(I)-catalyzed processes offers a significant contribution to existing strategies for laboratory-scale preparation of enantioenriched alpha-amidoboronates.
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