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

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 re...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-04, Vol.86 (7), p.5110-5119
Main Authors: Yang, Gao-feng, Li, Guang-xun, Huang, Jin, Fu, Ding-qiang, Nie, Xiao-kang, Cui, Xin, Zhao, Jin-zhong, Tang, Zhuo
Format: Article
Language:English
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Summary: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).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c03064