The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Ethyl indoline-2-carboxylate( cas:50501-07-0 ) is researched.Reference of Ethyl indoline-2-carboxylate.Min, Chang; Seidel, Daniel published the article 《Stereochemically Rich Polycyclic Amines from the Kinetic Resolution of Indolines through Intramolecular Povarov Reactions》 about this compound( cas:50501-07-0 ) in Chemistry – A European Journal. Keywords: chromenopyrroloquinoline tetrahydro aryl stereoselective preparation; indoline kinetic resolution diastereoselective enantioselective Povarov cinnamyloxy benzaldehyde; asymmetric catalysis; chiral phosphoric acids; cycloaddition; kinetic resolution; organocatalysis. Let’s learn more about this compound (cas:50501-07-0).
Under control of a chiral Bronsted acid catalyst, racemic indolines I (R1 = H, 4-Me, 5-Br, 5-F, 5-MeO; R2 = Me, EtO2C, Ph, 4-MeOC6H4, etc.) underwent intramol. Povarov reactions with achiral aromatic aldehydes II (R3 = Ph, 3-ClC6H4, 4-MeC6H4, 1-naphthyl, etc.; R4 = H, 5-Br, 3-MeO, etc.) bearing a pendent dienophile. One enantiomer of the indoline reacted preferentially, resulting in the highly enantio- and diastereoselective formation of polycyclic heterocycles III with four stereogenic centers. This kinetic resolution approach exploits the differential formation/reactivity of diastereomeric ion pairs.
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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics