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Cascade Reductive Rearrangement for the Stereoselective Synthesis of Multifunctional Piperidinones: A Combined Experimental and Computational Study
Author(s) -
Zhu Guoxun,
Ma Lei,
Zhang Kaixin,
Zhou Zhi,
Song Huacan,
Yi Wei
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201904106
Subject(s) - stereoselectivity , cascade , imine , combinatorial chemistry , chemistry , cascade reaction , stereochemistry , organic chemistry , catalysis , chromatography
An efficient and practical reductive rearrangement reaction has been developed for the stereoselective synthesis of diverse piperidinones. This transformation features mild conditions, good substrate/functional group compatibility and large‐scale synthetic potential. Subsequent combined DFT and experimental studies revealed a reduction triggered cascade pathway in which the active imine species was involved as the key intermediate. The biological application of the products has also been demonstrated by acting as the potent antitumor agents, which further strengthens the synthetic utility of this approach.