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. 2014 Jul 1;53(27):6974-7.
doi: 10.1002/anie.201400946. Epub 2014 May 19.

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

Hidefumi Nakatsuji  1 , Yasuhiro Sawamura, Akira Sakakura, Kazuaki Ishihara
Affiliations

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

Hidefumi Nakatsuji et al. Angew Chem Int Ed Engl. .

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.

Keywords: asymmetric catalysis; cyclization; iodine; lactones; organocatalysis.

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