Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 6, Pages 1645-1649Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201709823
Keywords
amination; enantioselectivity; fluorination; N-heterocyclic carbenes; organocatalysis
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Funding
- A*STAR SERC [R-143-000-648-305]
- Ministry of Education of Singapore [R-143-000-613-112]
- Singapore EDB
- GlaxoSmithKline [R-143-000-564-592]
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Described is an unprecedented NHC-catalyzed (NHC = N-heterocyclic carbene), stereoselective ring opening of epoxy and cyclopropyl enals to deliver valuable compounds bearing multiple stereocenters. A straightforward three-step procedure involving two catalytic enantioselective transformations has been developed and leads to a regio- and stereodivergent synthesis of either 1,2-amino alcohols/diamines or 1,4-fluoro alcohols with excellent diastereo- and enantiopurity.
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