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Silver‐Catalyzed Epoxidation of Aldehydes Using Donor‐/ Acceptor‐type Vinyl Diazosuccinimides to Access Spiro‐Pyrrolidinedioneoxiranes
Author(s) -
Laha Debasish,
Bhat Ramakrishna G.
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000123
Subject(s) - chemistry , catalysis , acceptor , substrate (aquarium) , carbenoid , electron donor , organic chemistry , combinatorial chemistry , rhodium , physics , oceanography , geology , condensed matter physics
A silver(I)‐catalyzed method to access spiro‐pyrrolidinedioneoxiranes has been developed. Silver hexafluoroantimonate was found to be an efficient catalyst for the epoxidation of aldehydes using donor‐/acceptor‐substituted vinyl diazosuccinimides as carbenoid precursors. The protocol has been found to be highly regio‐ and chemoselective, and works well with aromatic aldehydes containing electron‐withdrawing and ‐donating groups to afford spiro‐pyrrolidinedioneoxiranes with a broad substrate scope.