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Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines

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Abstract

An Ir-catalyzed intramolecular asymmetric reductive amination (ARA) of bridged biaryl derivatives has been described. Using this unprecedented approach, synthetically useful dibenz[c,e]azepines containing both central and axial chiralities are obtained with excellent enantiocontrol (up to 97% ee). This methodology represents a rare example of enantioselective chemocatalytic synthesis of chiral dibenz[c,e]azepines featuring a broad substrate scope, and their synthetic utilities are exhibited by derivatizing the products into a chiral amino acid derivative and chiral phosphoramidite ligands, which display excellent enantiocontrol in Rh-catalyzed asymmetric hydrogenation of α-dehydroamino acid derivatives. Remarkably, our method is also applicable to enantioselectively synthesize an allocolchicine analogue.

Graphical abstract: Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines

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Publication details

The article was received on 09 Oct 2018, accepted on 21 Dec 2018 and first published on 27 Dec 2018


Article type: Edge Article
DOI: 10.1039/C8SC04482A
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines

    T. Yang, X. Guo, Q. Yin and X. Zhang, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC04482A

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