218933-58-5Relevant academic research and scientific papers
Stereoselective diazoalkane cycloadditions to chiral 5-alkylidene-1,3- dioxan-4-ones and 3-benzylidene-β-lactones
Bartels, Annett,Jones, Peter G.,Liebscher, Juergen
, p. 1645 - 1654 (1998)
Stereoselective 1,3-dipolar cycloaddition of diazoalkanes to (E)-5- alkylidene-1,3-dioxan-4-ones 1 and the (Z)-isomers (Z)-I afforded spiropyrazolines 3 and 10, respectively. The optically active 2-benzylidene- 3-methyl-β-lactone (8) was synthesized from the corresponding 5-benzylidene- 1,3-dioxan-4-one 1f by hydrolysis and recyclization and added diazomethane with opposite stereodifferentiation. Photochemical elimination of nitrogen from spiropyrazolines 3 gave enantiomerically pure spirocyclopropanes 12 that could be further transformed to cyclopropanecarboxylic acids 13 and derivatives 14.
