Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 39, Pages 17049-17054Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202006137
Keywords
allenes; conjugate addition; enantioselectivity; organocatalysis; synthetic methods
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Funding
- National Natural Science Foundation of China [91956114]
- Research Grants Council of Hong Kong [16302617, 16302318]
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An organocatalytic enantioconvergent synthesis of chiral tetrasubstituted allenes is disclosed. With suitable chiral phosphoric acid catalysts, a range of racemic indole-substituted propargylic alcohols reacted with nucleophiles to provide efficient access to a series of enantioenriched allenes with high enantioselectivities. Control experiments suggested a mechanism involving remotely controlled asymmetric 1,8-addition of the in situ generated indole imine methide via a bifunctional transition state.
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