Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine |
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Authors: | Wang Mang Gao Lian Xun Mai Wen Peng Xia Ai Xiang Wang Fang Zhang Suo Bo |
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Institution: | State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Science, Changchun, 130022, P. R. China. |
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Abstract: | Chiral quaternary ammonium salts derived from cinchonidine have been applied to catalyze the stereoselective iodolactonizations of trans-5-aryl-4-pentenoic acids leading to a mixture of two regioselectively iodolactonized products with fair to excellent yield (37-98%) and moderate enantioselectivity (exo = 42.0% ee, endo = 31.0% ee) under mild conditions. This work is the first example of asymmetric iodolactonization reaction in the presence of less than a stoichiometric amount of chiral reagent. |
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