| Summary: | 碩士 === 國立臺灣師範大學 === 化學系 === 101 === Using phosphine catalyzed [3+2] annulation to obtain functionalized spirocyclic
cyclopentenes which has regioselectivity. 1,3-indandione is an important constituent
functional group of natural product. And some derived molecules have biological
activity. 2-arylidene-1,3-indandione can be obtained by domino Knoevenagel
condensation of 1,3-indandione and aromatic aldehyde in a single one-pot operation.
At room temperature and under nitrogen atmosphere, 2-arylidene-1,3-indandione with
ethyl-2,3-butadienoate dissolved in toluene, and catalyzed by triphenylphosphine,
then doing [3+2] annulation. The starting materials are either electron-donating or
electron-withdrawing group, the products both have good regioselectivity (up to 5:1)
and yields (63-99%). To the best of our knowledge this is the first report for the
synthesis of functionalized cyclopentenes using 2-arylidene-1,3-indandione and
ethyl-2,3-butadienoate.
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