Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 9, Issue 12, Pages 3511-3517Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201402865
Keywords
asymmetric synthesis; bromolactonization; carboxylic acids; desymmetrization; organocatalysis
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Funding
- MEXT
- Grants-in-Aid for Scientific Research [26105734, 23390005, 24659005, 25460014] Funding Source: KAKEN
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The results of studies leading to the development of enantioselective desymmetrizing, bromolactonization reactions of symmetric olefinic dicarboxylic acids, which are promoted by a C-3-symmetric trisimidazoline catalyst, are described. These processes generated carboxylic-acid-containing bromolactones in moderately high enantiomeric excesses. The results of optimization studies showed that reactions in a mixed solvent system of toluene and acetone proceeded with the highest levels of enantioselectivity. NMR studies probing the interactions between the catalyst and dicarboxylic acid substrates, as well as the effect of acetone on the stereochemistry of the process, are also described.
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