Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 45, Pages 16119-16123Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910008
Keywords
asymmetric catalysis; enantioselectivity; ketimines; P ligands; rhodium
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Funding
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- CAS [QYZDY-SSW-SLH029]
- NSFC [21725205, 21432007, 21572246]
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Highly enantioselective rhodium-catalyzed addition of arylboroxines to N-unprotected ketimines is realized for the first time by employing chiral BIBOP-type ligands with a Rh loading as low as 1 mol %. A range of chiral alpha-trifluoromethyl-alpha,alpha-diaryl alpha-tertiary amines or 3-amino-3-aryloxindoles were formed with excellent ee values and yields by employing either WingPhos or PFBO-BIBOP as the ligand. The method has enabled an efficient enantioselective synthesis of cipargamin.
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