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Cooperative activation with chiral nucleophilic catalysts and N-haloimides: enantioselective iodolactonization of 4-arylmethyl-4-pentenoic acids. | LitMetric

Cooperative activation with chiral nucleophilic catalysts and N-haloimides: enantioselective iodolactonization of 4-arylmethyl-4-pentenoic acids.

Angew Chem Int Ed Engl

Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603 (Japan) http://www.ishihara-lab.net.

Published: July 2014

AI Article Synopsis

  • * N-Chlorophthalimide (NCP) acts as a Lewis acid that activates and oxidizes iodine (I2) to facilitate this iodolactonization process.
  • * Only 0.5 equivalents of I2 are needed when combined with 1.5 equivalents of NCP to produce the required iodinating reagent for the reaction.

Article Abstract

Chiral triaryl phosphates promote the enantioselective iodolactonization of 4-substituted 4-pentenoic acids to give the corresponding iodolactones in high yields with high enantioselectivity. N-Chlorophthalimide (NCP) is employed as a Lewis acidic activator and oxidant of I2 for the present iodolactonization. In combination with 1.5 equivalents of NCP, only 0.5 equivalents of I2 are sufficient to generate the iodinating reagent.

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Source
http://dx.doi.org/10.1002/anie.201400946DOI Listing

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