Stereochemically Rich Polycyclic Amines from the Kinetic Resolution of Indolines through Intramolecular Povarov Reactions |
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| Authors: | Chang Min Prof. Dr. Daniel Seidel |
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| Affiliation: | 1. http://seidel‐group.com/;2. Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ, USA |
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| Abstract: | Under control of a chiral Brønsted acid catalyst, racemic indolines undergo intramolecular Povarov reactions with achiral aromatic aldehydes bearing a pendent dienophile. One enantiomer of the indoline reacts preferentially, resulting in the highly enantio‐ and diastereoselective formation of polycyclic heterocycles with four stereogenic centers. This kinetic resolution approach exploits the differential formation/reactivity of diastereomeric ion pairs. |
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| Keywords: | asymmetric catalysis chiral phosphoric acids cycloaddition kinetic resolution organocatalysis |
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