Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 43, Pages 15334-15338Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908923
Keywords
allenes; annulations; atropisomer; organocatalysis; synthetic methods
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Funding
- National Science Foundation of China [21472042, 21772016]
- Jiangsu Province Funds for Distinguished Young Scientists [BK20160005]
- Shanghai Municipal Education Commission [2019-01-07-00-10-E00072]
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Although asymmetric phosphine catalysis is a powerful tool for the construction of various chiral carbon centers, its synthetic potential toward an enantioenriched atropisomer has not been explored yet. Reported herein is a phosphine-catalyzed atroposelective (4+2) annulation of delta-acetoxy allenoates and 2-hydroxyquinone derivatives. The reaction provides expedient access to aryl-naphthaquinone atropisomers by the de novo construction of a benzene ring. The two functionalities of the catalyst, a tertiary phosphine (Lewis base) and a tertiary amine (Bronsted base), cooperatively enable this process with high regio- and enantioselectivities.
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