Brønsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo‐ and Enantioselective Synthesis of Spirolactams

• Published in: Angewandte Chemie International Edition Vol. 60; no. 52; pp. 27164 - 27170
• Main Authors: Chen, Peng‐Fei, Zhou, Bo, Wu, Peng, Wang, Binju, Ye, Long‐Wu
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 20.12.2021; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: alkynes; Aromatic compounds; Atom economy; Brønsted acids; Catalysis; Chemistry; Chemistry, Multidisciplinary; cyclizations; Enantiomers; heterocycles; Heterocyclic compounds; kinetic resolution; Nucleotide sequence; Phosphoric acid; Physical Sciences; Science & Technology; Substrates; ASYMMETRIC-SYNTHESIS; HYDROGENATION; alkynes; OXINDOLES; CLAISEN REARRANGEMENT; INDOLES; cyclizations; YNAMIDES; REDUCTION; heterocycles; kinetic resolution; INHIBITORS; Bronsted acids; ACCESS; Brønsted acids

Described herein is a novel Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom‐economic synthesis of a range of valuable spirolactams from readily available ynamides in generally good to excellent yields with excellent diastereoselectiviti...