期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 10, 页码 2725-2729出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611181
关键词
asymmetric catalysis; enantioselectivity; iridium; reductive amination; tetrahydroisoquinolines
资金
- National Natural Science Foundation of China [21402155]
- Yangling Bureau of Science and Technology [2016NY-25]
- Northwest AF University [Z109021521]
A one-pot N-Boc deprotection and catalytic intramolecular reductive amination protocol for the preparation of enantiomerically pure tetrahydroisoquinoline alkaloids is described. The iodine-bridged dimeric iridium complexes displayed superb stereoselectivity to give tetrahydroisoquinolines, including several key pharmaceutical drug intermediates, in excellent yields under mild reaction conditions. Three additives played important roles in this reaction: Titanium(IV) isopropoxide and molecular iodine accelerated the transformation of the intermediate imine to the tetrahydroisoquinoline product; p-toluenesulfonic acid contributed to the stereocontrol.
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