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Copper‐Catalyzed Formation of α‐Alkoxycycloalkenones from N ‐Tosylhydrazones
Author(s) -
Su Naijing,
Theorell Juliana A.,
Wink Donald J.,
Driver Tom G.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201505993
Subject(s) - copper , chemistry , cycloaddition , carbenoid , catalysis , iodide , lithium (medication) , lewis acids and bases , alkyl , alkoxy group , medicinal chemistry , organic chemistry , rhodium , medicine , endocrinology
The combination of 20 mol % of copper iodide and lithium tert ‐butoxide triggers the formation of a broad range of substituted, functionalized α‐alkoxy 2 H ‐naphthalenones from readily available N ‐tosylhydrazones. The data suggests that this transformation occurs through cycloaddition of a copper carbenoid with an ester, followed by a Lewis acid‐catalyzed [1,2] alkyl shift of the in situ generated alkoxyepoxide intermediate.