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Phosphoric Acid Catalyzed Asymmetric [2+2] Cyclization/Penicillin–Penillonic Acid Rearrangement
Author(s) -
Zhang Ming,
Yu Changjun,
Xie Junqiu,
Xun Xudong,
Sun Wangsheng,
Hong Liang,
Wang Rui
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201712571
Subject(s) - phosphoric acid , enantioselective synthesis , chemistry , catalysis , penicillin , cycloaddition , organocatalysis , combinatorial chemistry , lactam , organic chemistry , stereochemistry , medicinal chemistry , antibiotics , biochemistry
Abstract Enantioselective synthesis of imidazolidin‐5‐ones through a phosphoric acid catalyzed reaction between azlactones and N‐substituted β‐carbolines is reported. The reaction takes place via an initial formal [2+2] cycloaddition to generate an α‐amino‐β‐lactam, which subsequently undergoes an acid‐catalyzed asymmetric penicillin–penillonic acid (PPA) rearrangement with high diastereo‐ and enantioselectivity. To the best of our knowledge, this represents the first [2+2] cyclization of azlactones with imines and the first asymmetric PPA rearrangement, which are linked together by the phosphoric acid catalyst.