Yttrium‐Catalyzed Intramolecular Hydroalkoxylation/Claisen Rearrangement Sequence: Efficient Synthesis of Medium‐Sized Lactams

• Published in: Angewandte Chemie International Edition Vol. 56; no. 14; pp. 4015 - 4019
• Main Authors: Zhou, Bo, Li, Long, Zhu, Xin‐Qi, Yan, Juan‐Zhu, Guo, Yi‐Lin, Ye, Long‐Wu
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 27.03.2017; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Cascade chemical reactions; Chemistry; Chemistry, Multidisciplinary; cyclization; heterocycles; homogeneous catalysis; Physical Sciences; rearrangements; Science & Technology; Yttrium; ELECTROPHILIC REARRANGEMENTS; GOLD CATALYSIS; CHIRAL YNAMIDES; C-H FUNCTIONALIZATION; ALKYNES; cyclization; CASCADE REACTION; ETHERS; CLAISEN-TYPE REARRANGEMENT; homogeneous catalysis; yttrium; RING-CLOSING METATHESIS; LACTONES; heterocycles; rearrangements
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201700596

An efficient yttrium‐catalyzed intramolecular hydroalkoxylation/Claisen rearrangement sequence has been achieved, thus enabling facile access to a diverse array of valuable medium‐sized lactams. Furthermore, a mechanistic rationale for this novel cascade reaction is well supported by a variety of control experiments. Ring maker: An efficient yttrium‐catalyzed tandem intramolecular hydroxyalkylation/Claisen rearrangement has been achieved, enabling facile access to a diverse array of valuable medium‐sized lactams. A mechanistic rationale for this novel reaction sequence is well supported by a variety of control experiments.