Cooperative Activation with Chiral Nucleophilic Catalysts and  N ‐Haloimides: Enantioselective Iodolactonization of 4‐Arylmethyl‐4‐pentenoic Acids | Zendy

Nakatsuji Hidefumi | Zendy; Sawamura Yasuhiro | Zendy; Sakakura Akira | Zendy; Ishihara Kazuaki | Zendy

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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.

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