ArticleAngewandte Chemie (International ed. in English)2016
Synthesis of Enantioenriched Indolines by a Conjugate Addition/Asymmetric Protonation/Aza-Prins Cascade Reaction.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Organocatalytic Synthesis of α-Trifluoromethyl Allylboronic Acids by Enantioselective 1,2-Borotropic Migration.Journal of the American Chemical Society · 2020Article
- Evaluation of the photodecarbonylation of crystalline ketones for the installation of reverse prenyl groups on the pyrrolidinoindoline scaffold.Tetrahedron · 2020Article
- Recent Advances in Catalyzed Sequential Reactions and the Potential Use of Tetrapyrrolic Macrocycles as Catalysts.Molecules (Basel, Switzerland) · 2018Review
- Catalytic [2 + 2 + 2] cycloaddition with indium(iii)-activated formaldimines: a practical and selective access to hexahydropyrimidines and 1,3-diamines from alkenes.Chemical science · 2017Article
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Abstract
A conjugate addition/asymmetric protonation/aza-Prins cascade reaction has been developed for the enantioselective synthesis of fused polycyclic indolines. A catalyst system generated from ZrCl4 and 3,3'-dibromo-BINOL enables the synthesis of a range of polycyclic indolines in good yields and with high enantioselectivity. A key finding is the use of TMSCl and 2,6-dibromophenol as a stoichiometric source of HCl to facilitate catalyst turnover. This transformation is the first in which a ZrCl4 ⋅BINOL complex serves as a chiral Lewis-acid-assisted Brønsted acid.
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