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Cooperative Silver‐ and Base‐Catalyzed Diastereoselective Cycloaddition of Nitrones with Methylene Isocyanides: Access to 2‐Imidazolinones
Author(s) -
Chen Yan,
Wu Yijing,
Shatskiy Andrey,
Kan Yuhe,
Kärkäs Markus D.,
Liu JianQuan,
Wang XiangShan
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000437
Subject(s) - chemistry , cycloaddition , diastereomer , base (topology) , catalysis , methylene , combinatorial chemistry , reaction mechanism , medicinal chemistry , stereochemistry , organic chemistry , mathematical analysis , mathematics
A protocol involving cooperative silver‐ and base‐catalyzed diastereoselective cycloaddition of nitrones with isocyanides is described, providing access to a wide range of 2‐imidazolinone derivatives with various functional groups as single diastereomers. Varying the base and temperature of the reaction allowed selective access to both diastereomers of the product. A plausible reaction mechanism is proposed and supported by DFT calculations.