Electroreductive intramolecular coupling of phthalimides with aromatic aldehydes: application to the synthesis of lennoxamine.
The electroreductive intramolecular coupling of phthalimides with aromatic aldehydes in the presence of chlorotrimethylsilane and triethylamine led to five-, six-, and seven-membered cyclized products (58-84%). The electroreductive cyclization was applied to the total synthesis of lennoxamine.
Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101, Koyama-cho Minami, Tottori 680-8552, Japan. kise@bio.tottori-u.ac.jp
Naoki
N
Kise
Shinsaku
S
Isemoto
Toshihiko
T
Sakurai
D000447:Aldehydes / Q000737:chemistry*; D004146:Dioxanes / Q000138:chemical synthesis* / Q000737:chemistry; D004563:Electrochemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010797:Phthalimides / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D004146:Dioxanes; D010797:Phthalimides; C442893:lennoxamine