237427-27-9Relevant academic research and scientific papers
Rhodium carbenoid-initiated Claisen rearrangement: scope and mechanistic observations.
Wood,Moniz
, p. 371 - 374 (2008/02/13)
[formula: see text] It has been shown that alpha-diazoketones react with allylic alcohols in the presence of Rh(II) catalysts to furnish intermediate enols which subsequently undergo Claisen rearrangement to alpha-hydroxyketones. Herein we report (1) studies into the mechanism of this transformation which establish that Claisen rearrangement is neither rhodium- nor acid-catalyzed but a reaction intrinsic to the intermediate enols that proceeds at a rate governed by enol substituents (R3, R4, R5) and (2) the reaction of alpha-diazoketones with propargylic alcohols and preliminary investigations into its scope and mechanism.
Facile preparation of allenic hydroxyketones via rearrangement of propargylic alcohols
Jung, Michael E.,Pontillo, Joseph
, p. 367 - 369 (2008/02/11)
(equation presented) Treatment of tertiary propargylic alcohols 13 with 3-diazo-2-butanone 6 and catalytic dirhodium tetraacetate in benzene gave good yields of the diastereomeric allenic hydroxyketones 14, with, in some cases, good diastereocontrol. Thes
