Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 42, Pages 15104-15110Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908279
Keywords
asymmetric catalysis; atropisomer-selectivity; axial chirality; enantioselectivity; o-hydroxybenzyl alcohols
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Funding
- NSFC [21772069, 21831007]
- Six Kinds of Talents Project of Jiangsu Province [SWYY-025]
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A new strategy for enantioselective synthesis of axially chiral naphthyl-indoles has been established through catalytic asymmetric addition reactions of racemic naphthyl-indoles with bulky electrophiles. Under chiral phosphoric acid catalysis, azodicarboxylates and o-hydroxybenzyl alcohols served as bulky but reactive electrophiles that were attacked by C2-unsubstituted naphthyl-indoles, which underwent a dynamic kinetic resolution to afford two series of axially chiral naphthyl-indoles in good yields (up to 98 %) and high enantioselectivities (up to 98:2 er).
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