Forging Fluorine-Containing Quaternary Stereocenters by a Light-Driven Organocatalytic Aldol Desymmetrization Process
Reported herein is a light-triggered organocatalytic strategy for the desymmetrization of achiral 2-fluoro-substituted cyclopentane-1,3-diketones. The chemistry is based on an intermolecular aldol reaction of photochemically generated hydroxy-o-quinodimethanes and simultaneously forges two adjacent fully substituted carbon stereocenters, with one bearing a stereogenic carbon–fluorine unit. The method uses readily available substrates, a simple chiral organocatalyst, and mild reaction conditions to afford an array of highly functionalized chiral 2-fluoro-3-hydroxycyclopentanones.
A Convenient Synthesis of Spirodione and 2,2-Disubstituted Cyclopentane-1,3-dione System
An efficient, one pot strategy for the synthesis of spirodione and 2,2-disubstituted cyclopentane-1,3-dione has been developed by using ketals and 1,2-disilyloxycyclobutene in the presence of excess BF3*Et2O.
Pandey, Bipin,Khire, Uday R.,Ayyangar, Nagaraj R.
p. 2741 - 2748
(2007/10/02)
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