Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 45, Pages 14736-14741Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809692
Keywords
asymmetric synthesis; chiral palladium enolates; chromans; cooperative catalysis; quinone methides
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Funding
- Deutsche Forschungsgemeinschaft [SCHN 441/11-2]
- Fonds der Chemischen Industrie
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We describe herein a conceptually novel, cooperative Bronsted acid/base catalyzed process for the conjugate addition of cyclic beta-keto esters to ortho-quinone methides both generated in situ. Upon hemiacetalization, densely functionalized chiral chromans with two adjacent quaternary and additionally a tertiary stereogenic center were obtained with very good diastereoselectivity (up to >95:5 d.r.) and typically excellent enantioselectivity (up to >99% ee). The striking feature and key to success is the dual catalytic activation of both nucleophile and electrophile in two separate cycles with a single chiral catalyst.
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