Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 5, Pages 2039-2043Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201912882
Keywords
allylic alkylation; asymmetric catalysis; fluorination; iridium; stereodivergent synthesis
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Funding
- National Key Research and Development Program of China [2016YFA0202900]
- NSFC [21821002, 21572252, 91856201]
- Chinese Academy of Sciences [XDB20000000, QYZDY-SSW-SLH012]
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The stereodivergent iridium-catalyzed allylic alkylation and fluorination of acyclic ketones is described. alpha-Pyridyl-alpha-fluoroketones with vicinal tertiary and quaternary stereocenters were obtained in moderate to excellent yields and stereoselectivities. Distinct from known stereodivergent synthesis, for which two different chiral catalysts are required in general, herein we report a sequence-dependent stereodivergent synthesis. With only a single chiral Ir catalyst, all four possible stereoisomers of the products were prepared from the same starting materials by simply adjusting the sequence of asymmetric allylic alkylation and fluorination and varying the absolute configuration of the Ir catalyst.
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