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Exploring the Metal‐Catalyzed Reactions of α‐Diazo‐β‐hydroxyamino Esters: Conversion of Cyclic Aldonitrones into Ketonitrones
Author(s) -
Lieou Kui Evelyn,
Kanazawa Alice,
Philouze Christian,
Poisson JeanFrançois,
Py Sandrine
Publication year - 2017
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.201601255
Subject(s) - diazo , chemistry , carbenoid , catalysis , ethyl diazoacetate , metal , combinatorial chemistry , hydride , transformation (genetics) , medicinal chemistry , organic chemistry , cyclopropanation , rhodium , biochemistry , gene
α‐Diazo β‐hydroxyamino esters, readily obtained by the addition of lithiated ethyl diazoacetate to cyclic nitrones, react smoothly in the presence of metal catalysts to produce ketonitrones. This transformation results from a selective 1,2‐hydride shift of the metal carbenoid intermediates. The process is particularly efficient for diazo‐ N ‐hydroxypyrrolidine systems. For diazo‐ N ‐hydroxypiperidine substrates, C–H insertion can be a competitive reaction.