Preparation of tethered aldehyde ynoates and ynones by ring fragmentation of cyclic gamma-oxy-beta-hydroxy-alpha-diazo carbonyls.
Cyclic gamma-oxy-beta-hydroxy-alpha-diazo carbonyls undergo Lewis acid induced ring fragmentation to provide either ynoates or ynones tethered to an aldehyde, ketone, or ester. The fragmentation precursors are convenient to prepare by adding lithiated alpha-diazo carbonyls to alpha-oxy ketones. The fragmentation appears general and provides a variety of functional group-rich products in good to excellent yield.
Bayir
Ali
A
Department of Chemistry, The University of Vermont, 82 University Place, Burlington, Vermont 05405, USA.
Draghici
Cristian
C
Brewer
Matthias
M