ArticleThe Journal of organic chemistry2012
Palladium(II)-catalyzed enantioselective synthesis of 2-vinyl oxygen heterocycles.
Article in The Journal of organic chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Asymmetric synthesis of chiral (thio)chromanes and exploration on their structure-activity relationship in macrophages.RSC advances · 2023Article
- Stereochemistry of Chiral 2-Substituted Chromanes: Twist of the Dihydropyran Ring and Specific Optical Rotation.Molecules (Basel, Switzerland) · 2023Article
- Catalytic Asymmetric β-Oxygen Elimination.Angewandte Chemie (International ed. in English) · 2022Article
- Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications.Chemical reviews · 2021Article
- Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling.Angewandte Chemie (International ed. in English) · 2020Article
- Chiral Brønsted acid-catalyzed intramolecular SChemical science · 2018Article
- Article
- Terminal olefins to chromans, isochromans, and pyrans via allylic C-H oxidation.Journal of the American Chemical Society · 2014Article
- Enantioselective synthesis and application to the allylic imidate rearrangement of amine-coordinated palladacycle catalysts of cobalt sandwich complexes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2013Article
- Catalytic platinum-initiated cation-olefin reactions with alkene terminating groups.Chemical communications (Cambridge, England) · 2013Article
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Authors and funding
4 authors.
Funding
Abstract
2-Vinylchromanes (1), 2-vinyl-1,4-benzodioxanes (2), and 2,3-dihydro-2-vinyl-2H-1,4-benzoxazines (3) can be prepared in high yields (90-98%) and excellent enantiomeric purities (87-98% ee) by [COP-OAc](2)-catalyzed cyclization of phenolic (E)-allylic trichloroacetimidate precursors. Deuterium-labeling and computational experiments are consistent with these cyclization reactions taking place by an anti-oxypalladation/syn-deoxypalladation mechanism. 2-Vinylchromanes can also be prepared in good yields and high enantiomeric purities from analogous (E)-allylic acetate precursors, which constitutes the first report that acetate is a competent leaving group in COP-catalyzed enantioselective S(N)2' substitution reactions.
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