Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 7, Issue -, Pages -Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.70
Keywords
alkylidene cyclobutene; allene; allenyloxindole; chiral lanthanide shift reagent; chiral transfer
Categories
Funding
- National Science Foundation [NSF 0910597]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0910597] Funding Source: National Science Foundation
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A thermal [2 + 2] cycloaddition reaction of allene-ynes has been used to transform chiral non-racemic allenyl oxindoles into chiral non-racemic spirooxindoles containing an alkylidene cyclobutene moiety. The enantiomeric excesses were determined by chiral lanthanide shift NMR analysis and the transfer of chiral information from the allene to the spirooxindole was found to be greater than 95%.
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