Asymmetric Iodolactonization Utilizing Chiral Squaramides
- 13 November 2012
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 14 (23), 5884-5887
- https://doi.org/10.1021/ol302798g
Abstract
Asymmetric iodolactonization of γ- and δ-unsaturated carboxylic acids has been explored in the presence of six different chiral organocatalysts 5–8. The catalyst 6b was found to facilitate the cyclization of 5-arylhex-5-enoic acids 1 to the corresponding iodolactones 2 with up to 96% ee. By this protocol, unsaturated carboxylic acids are converted enantioselectively to synthetically useful δ-lactones in high yields using commercially available NIS. Apparently, both hydrogen bonding and aryl/aryl interactions are important for efficient stereodifferentiation.Keywords
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