210904-63-5Relevant academic research and scientific papers
Photochemical Ring Expansion of α-Alkoxycyclobutanones to 2-Acetoxy-5-alkoxytetrahydrofurans: Nucleophilic Reactions at the 2-Position
Umbricht, Gisela,Hellman, Melissa D.,Hegedus, Louis S.
, p. 5173 - 5178 (1998)
Photolysis of cyclobutanones in the presence of acetic acid produced 2-acetoxy-5-alkoxytetrahydro-furans regiospecifically and with retention of configuration at the migrating α-position. The acetoxy group was replaced by nucleophiles such as allylsilane, trimethylsilyl azide, diethylaluminum cyanide, and silylated thymine in the presence of Lewis acids.
Optically active cyclobutanone chemistry: synthesis of (-)-cyclobut-a and (±)-3′-epi-cyclobut-a
Brown, Brian,Hegedus, Louis S.
, p. 8012 - 8018 (2007/10/03)
The carbocyclic nucleoside analogues (-)-cyclobut-A and (±)-3′-epi-cyclobut-A were synthesized utilizing photolysis of the (benzyloxymethyl)(methoxy) chromium carbene complex 4 with optically active ene-carbamate 5 to produce the corresponding optically active α,α-disubstituted cyclobutanone 6. Stereoselective removal of the a-ethoxy group with inversion gave cyclobutanone 7, which was converted by existing methodology to the title compounds.
