Journal
CHEMICAL SCIENCE
Volume 10, Issue 8, Pages 2473-2477Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc04482a
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Funding
- Southern University of Science and Technology
- Shenzhen Science and Technology Innovation Committee [KQTD20150717103157174, JSGG20160608140847864, JCYJ20170817110055425]
- Shenzhen Nobel Prize Scientists Laboratory Project [C17783101]
- National Natural Science Foundation of China [21432007, 21801119]
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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 a-dehydroamino acid derivatives. Remarkably, our method is also applicable to enantioselectively synthesize an allocolchicine analogue.
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