Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 43, Pages 14193-14197Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809719
Keywords
asymmetric catalysis; asymmetric hydrogenation; chiral lactams; primary amines; reductive amination
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Funding
- Southern University of Science and Technology
- Shenzhen Science and Technology Innovation Committee [KQTD20150717103157174]
- Shenzhen Nobel Prize Scientists Laboratory Project [C17783101]
- National Natural Science Foundation of China [21432007, 21801119]
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A highly efficient ruthenium-catalyzed asymmetric reductive amination (ARA) of racemic -keto lactams with molecular hydrogen and ammonium salts is disclosed for the synthesis of enantiomerically pure primary amino lactams through dynamic kinetic resolution (DKR). By this approach, a range of syn primary -amino lactams were obtained in high yields with high chemo-, enantio-, and diastereoselectivity (up to 98% yield, 99%ee, >20:1 d.r., syn products). The utility of the products has been demonstrated by rapid access to a key synthetic intermediate towards biologically active drug molecules. Meanwhile, mechanistic studies and control experiments indicate that the reaction may proceed through the hydrogenation of an iminium intermediate.
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