期刊
SYNLETT
卷 30, 期 6, 页码 703-708出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611740
关键词
MBH adducts; aromatic amines; asymmetric allylic amination; nucleophilic amine catalysis; inorganic fluorides
资金
- National Science Foundation of China [21602018, 21272029]
- Jiangsu Overseas Visiting Scholar Program for University Prominent Young & Middle-Aged Teachers and Presidents
Asymmetric allylic amination of Morita-Baylis-Hillman (MBH) adducts with simple aromatic amines is successfully realized by nucleophilic amine catalysis. A range of substituted -methylene--arylamino esters is accessed in moderate to high yields (up to 88%) and with excellent enantioselectivities (up to 97% ee). Inorganic fluorides are found to be able to improve the enantioselectivity of the allylic amination reaction. A pyrrole-2-carboxylate and a cyclic imide are also compatible with this catalytic system. A chiral 2,3-dihydroquinolin-4-one derivative is easily obtained from the allylic amination product.
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