Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 22, Pages 8670-8674Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b01476
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Funding
- National Institute of Health [NIGMS R01GM063540]
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The development of an intermolecular and enantioselective aza-Wacker reaction is described. Using indoles as the N-source and a selection of alkenols as the coupling partners selective beta-hydride elimination toward the alcohol was achieved. This strategy preserves the newly formed stereocenter by preventing the formation of traditionally observed enamine products. Allylic and homoallylic alcohols with a variety of functional groups are compatible with the reaction in high enantioselectivity. Isotopic-labeling experiments support a syn aminopalladation mechanism for this new class of aza-Wacker reactions.
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