Regioselective, Diastereoselective, and Enantioselective One-Pot Tandem Reaction Based on an in Situ Formed Reductant: Preparation of 2,3-Disubstituted 1,5-Benzodiazepine.

Autor: Yang GF; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science, Chengdu, Sichuan, 610041, China.; University of Chinese Academy of Sciences, Beijing, 100049, China., Li GX; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science, Chengdu, Sichuan, 610041, China., Huang J; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science, Chengdu, Sichuan, 610041, China., Fu DQ; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science, Chengdu, Sichuan, 610041, China., Nie XK; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science, Chengdu, Sichuan, 610041, China., Cui X; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science, Chengdu, Sichuan, 610041, China., Zhao JZ; College of Art and Sciences, Shanxi Agricultural University, Taigu, Shanxi, 030800, China., Tang Z; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science, Chengdu, Sichuan, 610041, China.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2021 Apr 02; Vol. 86 (7), pp. 5110-5119. Date of Electronic Publication: 2021 Mar 16.
DOI: 10.1021/acs.joc.0c03064
Abstrakt: The 1,5-benzodiazepines are important skeletons frequently contained in medicinal chemistry. Herein, we described an unexpected tandem cyclization/transfer hydrogenation reaction for obtaining chiral 2,3-disubstituted 1,5-benzodiazepines. The enolizable aryl aldehydes were chosen as substrates to react with symmetric and unsymmetric o -phenylenediamines. The unforeseen tandem reaction occurred among many possible latent side reactions under chiral phosphoric acid catalysis and affords the corresponding products in moderate yields and regioselectivities, good diastereoselectivities, and enantiomeric ratio (up to 99:1).
Databáze: MEDLINE
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