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Cooperative Activation with Chiral Nucleophilic Catalysts and N ‐Haloimides: Enantioselective Iodolactonization of 4‐Arylmethyl‐4‐pentenoic Acids
Author(s) -
Nakatsuji Hidefumi,
Sawamura Yasuhiro,
Sakakura Akira,
Ishihara Kazuaki
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201400946
Subject(s) - enantioselective synthesis , chemistry , nucleophile , reagent , catalysis , organic chemistry , activator (genetics) , combinatorial chemistry , biochemistry , gene
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 I 2 for the present iodolactonization. In combination with 1.5 equivalents of NCP, only 0.5 equivalents of I 2 are sufficient to generate the iodinating reagent.